Acetone → 1-(6-methyl-3,4-dihydro-2H-pyran-2-yl)ethanol
Reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH:7]=[C:6]([CH3:10])[O:5]1)(=[O:3])[CH3:2].[BH4-].[Na+].CC(C)=O>C(O)C.O.C(=O)([O-])[O-].[K+].[K+]>[OH:3][CH:1]([CH:4]1[CH2:9][CH2:8][CH:7]=[C:6]([CH3:10])[O:5]1)[CH3:2]Participants
7
Procedure
A solution of 20.00 g of 16A in 40 ml of ethyl alcohol was added drop by drop to a solution of 2.71 g of sodium borohydride in 130 ml of ethyl alcohol and 65 ml of water, at 19°-23° C. After 30 minutes, 40 ml of acetone was added drop by drop. After 5 additional minutes, the reaction mixture was diluted with an equal volume of water, saturated with potassium carbonate, and extracted with ether. The extract was washed with saturated sodium chloride solution, dried (Na2SO4) and stripped of solvent. Some water remained in the residue. 100 ml of acetone was added to the residue; the solution was dried (Na2SO4) and stripped of solvent to give 2-(1-hydroxyethyl)-3,4-dihydro-6-methyl-2H-pyran (16B), as a liquid, b.p.: not determined.
Workup
- customat 19°-23° C
- extractionextracted with ether
- washThe extract was washed with saturated sodium chloride solution
- dry with materialdried (Na2SO4)
- addition100 ml of acetone was added to the residue
- dry with materialthe solution was dried (Na2SO4)
Sources & evidence
- ORD record
- ord-0562e6a8b1594123831fd1198790482a
- Source dataset
- uspto-grants-1983_06
- Patent number
- US04388104
Reaction notes
Loading…