Water → 4,4-dimethyl-3,4-dihydro-1H-isochromen-6-ol

HRID 716813Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][O:8][CH2:7][C:6]2([CH3:14])[CH3:13].BrB(Br)Br.O>C(Cl)Cl>[CH3:13][C:6]1([CH3:14])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([OH:2])[CH:4]=2)[CH2:9][O:8][CH2:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

6-methoxy-4,4-dimethyl-3,4-dihydro-1H-isochromene (Intermediate 41, 350 mg, 1.8205 mmol) was dissolved in DCM (10 mL) and the solution was cooled to 0° C. Tribromoborane (228.04 mg, 0.9102 mmol) was added and the resulting mixture was stirred at 0° C. for 2 hours. Water (10 mL) was added and the two phases were separated. Organics were dried over Na2SO4, filtered and dried in vacuo. The crude was purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 70:30 as eluent affording the title compound (42 mg).

Workup

customthe two phases were separated
dry with materialOrganics were dried over Na2SO4
filtrationfiltered
customdried in vacuo
customThe crude was purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 70:30 as eluent

Sources & evidence

ORD record: ord-08fb9b5bbbf14317a1cc6f6eabf354a4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193704B2

Reaction notes

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