Sodium borohydride → HCID 57565070, compound

HRID 1726865Notes

Reaction equation

HRID 1726865 reaction equation
[C:1]1([C:7]2([CH:14]=[O:15])[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([C:7]2([CH2:14][OH:15])[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57565084HCID 57565084, compound

Product 1

HCID 57565070HCID 57565070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (Z)-1-phenylcyclohept-4-enecarbaldehyde (22 mg, step C) in methanol (1 mL) was added sodium borohydride (8 mg), and the resulting mixture was stirred at room temperature for 1 h. Methanol was removed in vacuo, water and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo to give the title compound as an oil. 1H NMR (400 MHz, CDCl3) δ 1.91 (2H, m), 2.20 (6H, m), 3.55 (2H, s), 5.68 (2H, m), 7.35 (5H, m). 13C NMR (CDCl3, 100 MHz) δ 24.0, 32.9, 47.3, 71.7, 126.3, 127.4, 128.6, 131.2, 144.3.

Workup

  1. customMethanol was removed in vacuo, water and ethyl acetate
  2. additionwere added
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-ec1b5e22fe014bc7b69d84c5dd315300
Source dataset
uspto-grants-2009_02
Patent number
US07494986B2

Reaction notes

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