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

HRID 841750Notes

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% lEtOAc-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-c80f31c58a8346c7bc872b6b2586693d
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369261B1

Reaction notes

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