Ethyl Acetate → (1-Naphthalen-1-yl-cyclopentyl)-methanol

HRID 2169375Notes

Reaction equation

HRID 2169375 reaction equation
[C:1]1([C:11]2([CH:16]=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].C(OCC)(=O)C>CO.CCCCCC>[C:1]1([C:11]2([CH2:16][OH:17])[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 867260041-Naphthalen-1-yl-cyclopentanecarbaldehyde

Product 1

HCID 86726005(1-Naphthalen-1-yl-cyclopentyl)-methanolYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

A solution of 1-naphthalen-1-yl-cyclopentanecarbaldehyde (339) (10 g, 44.6 mmol) in methanol (150 mL) was cooled to 0° C. and NaBH4 (3.373 g, 89.2 mmol) was added in portions (8 portions). After the addition was completed the reaction mixture was allowed to stir at room temperature for 1 h (silica TLC, 10% ethyl acetate in hexane; Rf=0.3). The reaction mixture was quenched with aqueous NH4Cl solution and concentrated in vacuo as much as possible; diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic part was washed with brine (50 mL), dried and concentrated in vacuo to get a crude mass which was purified by CombiFlash using gradient eluent mixture of ethyl acetate and hexane to get pure (1-naphthalen-1-yl-cyclopentyl)-methanol (340) (8.75 g, 87%) as a white solid.

Workup

  1. additionAfter the addition
  2. customThe reaction mixture was quenched with aqueous NH4Cl solution
  3. concentrationconcentrated in vacuo as much as possible
  4. additiondiluted with water (100 mL)
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. washThe organic part was washed with brine (50 mL)
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto get a crude mass which
  10. customwas purified by CombiFlash
  11. additiongradient eluent mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-e97c1d41c3ab45fab97743e21e9c19ee
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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