Sodium borohydride → HCID 86678082, compound

HRID 2274707Notes

Reaction equation

HRID 2274707 reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[BH4-].[Na+]>CO>[OH:1][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86678083HCID 86678083, compound

Product 1

HCID 86678082HCID 86678082, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A cooled (0° C.) solution of (11Z,14Z)-methyl 3-oxoicosa-11,14-dienoate (2) (3.5 g, 10.4 mmol) in dry methanol (75 mL) was treated with NaBH4 (787 mg, 20.8 mmol) and stirred (20 min). The reaction mixture was quenched by the careful addition of HCl (5%, aq.) in an equal volume of ice and extracted with CH2Cl2. The combined organic extracts were dried (Na2SO4), filtered, concentrated and the residue was subjected to flash chromatography (2%→10% EtOAc-hexanes) to yield (11Z,14Z)-methyl 3-hydroxyicosa-11,14-dienoate (3) (2.51 g, 71%) as a pale yellow oil. Rf 0.37 (30% EtOAc-hexanes). FW 338.51, C21H38O3.

Workup

  1. customThe reaction mixture was quenched by the careful addition of HCl (5%, aq.) in an equal volume of ice
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8067ab5ccdae4b1dac05906edab1292f
Source dataset
uspto-grants-2015_09
Patent number
US09126966B2

Reaction notes

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