Sodium borohydride → 2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid methyl ester

HRID 1047894Notes

Reaction equation

HRID 1047894 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[C:6]([CH3:12])[C:5]=1[O:13][CH:14]1[CH2:17][CH2:16][CH2:15]1.[BH4-].[Na+]>CCCCCC>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([CH3:12])[C:5]=1[O:13][CH:14]1[CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 593142392-Cyclobutoxy-5-formyl-3-methyl-benzoic acid methyl ester

Product 1

HCID 593140822-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid methyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-cyclobutoxy-5-formyl-3-methyl-benzoic acid methyl ester (676 mg, 2.7 mmol), silica gel (5.15 g) and NaBH4 (103 mg, 2.7 mmol) in hexane (30 mL) is heated at 40° C. overnight. The mixture is cooled to RT and filtered, washing the solids with EtOAc (15 mL) and diethyl ether (15 mL). The filtrate is concentrated in vacuo to give product (283) as viscous yellow oil (566 mg, 84%).

Workup

  1. temperatureThe mixture is cooled to RT
  2. filtrationfiltered
  3. washwashing the solids with EtOAc (15 mL) and diethyl ether (15 mL)
  4. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-aa9d54cd49b54462ba41a249d39edb05
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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