5-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid → (5-bromo-3,4-dihydro-1H-isochromen-1-yl)methanol

HRID 2173259Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12](O)=[O:13]>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[CH2:12][OH:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid (0.500 g, 1.94 mmol) in 1 mL of THF was added BH3. THF (3.88 mL, 3.88 mmol) drop wise at 0° C. The mixture was stirred at 0° C. for 2 h. The reaction was quenched with water and aqueous sodium hydroxide (1 N, 2 mL). The contents were stirred for 3 h, and then extracted with EtOAc. The organic layer was dried and concentrated to give (5-bromo-3,4-dihydro-1H-isochromen-1-yl)methanol 1H-NMR (400 MHz, CDCl3) δ 7.41 (t, J=2.4 Hz, 1H), 6.97˜7.04 (m, 2H), 4.75˜4.77 (m, 1H), 3.88˜3.92 (m, 1H), 3.73˜3.79 (m, 2H), 2.71-2.86 (m, 2H).

Workup

customwise at 0° C
customThe reaction was quenched with water and aqueous sodium hydroxide (1 N, 2 mL)
stirringThe contents were stirred for 3 h
extractionextracted with EtOAc
customThe organic layer was dried
concentrationconcentrated

Sources & evidence

ORD record: ord-4b02f2f794f8444ea05ff35d02d7123e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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