Sodium borohydride → Methyl [4-(5-hydroxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate

HRID 841509Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](=[O:23])[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[CH:19]([OH:23])[CH2:18][CH2:17][C:16]([CH3:24])([CH3:25])[C:15]=3[CH:14]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl[4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate (Compound 4) in 5 mL MeOH at 0° C. was added NaBH4 (18.0 mg, 0.48 mmol). The reaction was stirred at 0° C. for 2 hours and then quenched by the addition of H2O. The solution was diluted with Et2O and washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and the solvents were removed under reduced pressure. Column chromatography (20-40% EtOAc-hexanes) afforded 140.0 mg (87%) of the title compound as a colorless oil.

Workup

customquenched by the addition of H2O
additionThe solution was diluted with Et2O
washwashed with H2O and saturated aqueous NaCl
dry with materialbefore being dried (MgSO4)
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-b2b14c575dbd4553be36802283c71d00
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369225B1

Reaction notes

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