Sodium borohydride → HCID 58909483, compound

HRID 1985065Notes

Reaction equation

HRID 1985065 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][O:9][CH2:8][C:7]2=[O:14]>C(O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][O:9][CH2:8][CH:7]2[OH:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 454898026-Bromo-1H-2-benzopyran-4(3H)-one

Product 1

HCID 58909483HCID 58909483, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium borohydride (300 mg, 7.93 mmol) dissolved in a minimum amount of ice cold water was added dropwise at 0° C. to a solution of 6-Bromo-isochroman-4-one (1.49 g, 6.56 mmol) in absolute ethanol (27.0 mL). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The phases were separated and the organic phase washed with water and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to yield 6-Bromo-isochroman-4-ol (1.44 g, 95%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.40 (dd, J=8.3, 1.8 Hz, 1H), 7.30 (d, J=8.3 Hz, 1H), 7.15 (d, J=1.8 Hz, 1H), 4.63 (ABq, J=15.3 Hz, 2H), 4.49 (d, J=8.6 Hz, 1H), 4.07 (dd, J=12.0, 2.8 Hz, 1H), 3.83 (dd, J=12.0, 2.8 Hz, 1H), 2.60 (d, J=9.2 Hz, 1H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  2. customThe phases were separated
  3. washthe organic phase washed with water and saturated sodium chloride
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94f387cd4f0a4f8ba0608a466b4439f8
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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