Sodium borohydride → 4-Hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester

HRID 2092654Notes

Reaction equation

HRID 2092654 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:13][CH2:14][O:15][CH3:16])[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+]>CC(O)C>[CH2:1]([O:3][C:4]([C:6]1([CH2:13][CH2:14][O:15][CH3:16])[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58230138HCID 58230138, compound

Product 1

HCID 582299764-Hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(2-Methoxy-ethyl)-4-oxo-cyclohexanecarboxylic acid ethyl ester (1.60 g) was dissolved in 2-propanol (25 mL) The mixture was cooled to 0° C. and sodium borohydride (331 mg) was added in 3 portions over 10 minutes. Stirring was continued for 2 hours at 0° C. The reaction mixture was poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The title compound was obtained as an inseparable mixture of cis and trans diastereomeres (ratio: 3/1) as a light yellow liquid (1.58 g, 98%). This mixture was used without further purification. MS (EI)=230.0 [MH+].

Workup

  1. extractionextracted two times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e3783b7e48234d33b5208d2f5456d40e
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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