5-(hydroxymethyl)oxolane-2-carbonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The compounds of formula I wherein n is 0 are prepared by epoxidation-cyclization of novel cyanohydrins, i.e., 2-hydroxy-5-hexenenitrile or 2,5-dialkyl-2-hydroxy-5-hexenenitrile, of the formula ##STR3## wherein R1 and R2 are as defined for formula I, e.g., by epoxidation with m-chloroperbenzoic acid followed by treatment of the resulting epoxy cyanohydrin with hydrochloric acid to yield the novel 2-cyanotetrahydrofuran-5-methanol of the formula ##STR4## wherein R1 and R2 are as defined for formula I, and subsequent etherification e.g., with RCH2Cl. The 2-hydroxy-5-hexenenitriles are prepared by treating the corresponding unsaturated ketone with, acetic anhydride and potassium cyanide by the general procedure of R. Franks, R. Berry, and O. Shotwell, J. Am. Chem. Soc., 71, 3889 (1949). The unsaturated ketones are prepared by (1) reaction of an aldehyde with an unsaturated Grignard reagent followed by selective oxidation of the hydroxy group to a ketone, or (2) reaction of an allyl chloride with an alkanedione as described, for example, in F. Barbot, D. Mesnard, and L. Miginiac, Organic Preparations and Procedures International 10, 261 (1978).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The compounds of formula I wherein n is 0 are prepared by epoxidation-cyclization of novel cyanohydrins, i.e., 2-hydroxy-5-hexenenitrile or 2,5-dialkyl-2-hydroxy-5-hexenenitrile, of the formula ##STR3## wherein R1 and R2 are as defined for formula I, e.g., by epoxidation with m-chloroperbenzoic acid followed by treatment of the resulting epoxy cyanohydrin with hydrochloric acid to yield the novel 2-cyanotetrahydrofuran-5-methanol of the formula ##STR4## wherein R1 and R2 are as defined for formula I, and subsequent etherification e.g., with RCH2Cl. The 2-hydroxy-5-hexenenitriles are prepared by treating the corresponding unsaturated ketone with, acetic anhydride and potassium cyanide by the general procedure of R. Franks, R. Berry, and O. Shotwell, J. Am. Chem. Soc., 71, 3889 (1949). The unsaturated ketones are prepared by (1) reaction of an aldehyde with an unsaturated Grignard reagent followed by selective oxidation of the hydroxy group to a ketone, or (2) reaction of an allyl chloride with an alkanedione as described, for example, in F. Barbot, D. Mesnard, and L. Miginiac, Organic Preparations and Procedures International 10, 261 (1978).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The compounds of formula I wherein n is 0 are prepared by epoxidation-cyclization of novel cyanohydrins, i.e., 2-hydroxy-5-hexenenitrile or 2,5-dialkyl-2-hydroxy-5-hexenenitrile, of the formula ##STR3## wherein R1 and R2 are as defined for formula I, e.g., by epoxidation with m-chloroperbenzoic acid followed by treatment of the resulting epoxy cyanohydrin with hydrochloric acid to yield the novel 2-cyanotetrahydrofuran-5-methanol of the formula ##STR4## wherein R1 and R2 are as defined for formula I, and subsequent etherification e.g., with RCH2Cl. The 2-hydroxy-5-hexenenitriles are prepared by treating the corresponding unsaturated ketone with, acetic anhydride and potassium cyanide by the general procedure of R. Franks, R. Berry, and O. Shotwell, J. Am. Chem. Soc., 71, 3889 (1949). The unsaturated ketones are prepared by (1) reaction of an aldehyde with an unsaturated Grignard reagent followed by selective oxidation of the hydroxy group to a ketone, or (2) reaction of an allyl chloride with an alkanedione as described, for example, in F. Barbot, D. Mesnard, and L. Miginiac, Organic Preparations and Procedures International 10, 261 (1978).