Ethanol → (4S)-3,3-dimethyl-4-tetrahydropyranyloxy-1-hydroxymethylcyclohexene

HRID 1789246Notes

Reaction equation

HRID 1789246 reaction equation
[CH3:1][C:2]1([CH3:17])[C@@H:7]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH2:6][CH2:5][C:4]([CH:15]=[O:16])=[CH:3]1.C(O)C.[BH4-].[Na+]>O1CCCC1>[CH3:1][C:2]1([CH3:17])[C@@H:7]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH2:6][CH2:5][C:4]([CH2:15][OH:16])=[CH:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 13924111(4S)-3,3-dimethyl-4-tetrahydropyranyloxycyclohexene-1-carbaldehyde

Product 1

HCID 13924113(4S)-3,3-dimethyl-4-tetrahydropyranyloxy-1-hydroxymethylcyclohexeneYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4S)-3,3-dimethyl-4-tetrahydropyranyloxycyclohexene-1-carbaldehyde (8) (0.71 g, 2.98 mmoles) was dissolved in tetrahydrofuran (7 ml), and a 95% ethanol solution of sodium borohydride (0.38 g, 10 mmoles) was added dropwise over an ice bath. After the addition, the mixture was stirred for 2 hours at a temperature below 10° C. The solvent was evaporated under reduced pressure. The residue was diluted with water, and extracted twice with diethyl ether. The ethereal layer was dried over magnesium sulfate, filtered, concentrated, and purified by column chromatography (30 g of silica gel; n-hexane/ethyl acetate) to give 0.65 g (yield 91.3%) of a compound (9).

Workup

  1. additionAfter the addition
  2. customThe solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted twice with diethyl ether
  5. dry with materialThe ethereal layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography (30 g of silica gel; n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-421d6ba424f34877813e82a68e1fedb0
Source dataset
uspto-grants-1987_08
Patent number
US04687863

Reaction notes

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