Sodium borohydride → HCID 71061027, compound

HRID 1910997Notes

Reaction equation

HRID 1910997 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([C:12]([O:14][CH3:15])=[O:13])[C:10](=[O:11])[C:4]=2[CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]([OH:11])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71061071HCID 71061071, compound

Product 1

HCID 71061027HCID 71061027, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the crude methyl 3-bromo-5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate from step A2 (350 mg, 1.18 mmol) in MeOH (5 mL) was slowly added NaBH4 (44.6 mg, 1.18 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min. The solvent was removed in vacuo at rt. EtOAc (100 mL) was added and the organic layer was washed with water. The organic layer was concentrated, and the residue was purified using silica gel column chromatography (hexanes-60% EtOAc) to give methyl 3-bromo-5-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate (230 mg, 0.769 mmol, 65% yield). 1H NMR (500 MHz, chloroform-d) δ 7.81-7.39 (m, 1H), 7.35-7.23 (m, 1H), 7.01-6.87 (m, 1H), 5.13-4.96 (m, 1H), 3.77-3.65 (m, 3H), 3.39-3.22 (m, 1H), 3.20-2.56 (m, 3H), 2.47-1.86 (m, 3H), 1.65-1.30 (m, 1H).

Workup

  1. customat 0° C
  2. customThe solvent was removed in vacuo at rt
  3. additionEtOAc (100 mL) was added
  4. washthe organic layer was washed with water
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified

Sources & evidence

ORD record
ord-8f31dd889b924f6fb17ccbaa58baf28b
Source dataset
uspto-grants-2013_12
Patent number
US08604024B2

Reaction notes

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