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

HRID 51825Notes

Reaction equation

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

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-17e8658e25f640c7991e8aee5514b230
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713647B2

Reaction notes

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