(-)-(2S,3R)-1-propionyloxy-2,3-epoxy-8-methylnonane → (-)-(2S,3R)-2,3-epoxy-8-methyl-1-nonanol

HRID 249237Notes

Reaction equation

HRID 249237 reaction equation
C([O:5][CH2:6][C@@H:7]1[O:16][C@@H:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])(=O)CC.[OH-].[K+].CO>>[O:16]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C@@H:7]1[CH2:6][OH:5]

Participants

3

Reactant 2

HCID 14102164(-)-(2S,3R)-1-propionyloxy-2,3-epoxy-8-methylnonaneHCID 23689386Potassium hydroxide methanol

Product 1

HCID 14102158(-)-(2S,3R)-2,3-epoxy-8-methyl-1-nonanolYield 93.6%

Procedure

3.4 g of (-)-(2S,3R)-1-propionyloxy-2,3-epoxy-8-methylnonane was hydrolyzed with potassium hydroxide/methanol to yield 2.4 g of (-)-(2S,3R)-2,3-epoxy-8-methyl-1-nonanol.

Sources & evidence

ORD record
ord-f091f1539f854af4b358ec85ba1ccf23
Source dataset
uspto-grants-1993_05
Patent number
US05213975

Reaction notes

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