Borane;tetrahydrofuran → (5-bromo-3,4-dihydro-1H-isochromen-1-yl)methanol

HRID 1474283Notes

Reaction equation

HRID 1474283 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].B.C1COCC1>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

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 666464675-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid

Product 1

HCID 66646784(5-bromo-3,4-dihydro-1H-isochromen-1-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

Workup

  1. customThe reaction was quenched with water and aqueous sodium hydroxide (1 N, 2 mL)
  2. stirringThe contents were stirred for 3 h
  3. extractionextracted with EtOAc
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-939629442abf4ce18e2b0aecee610572
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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