Sodium borohydride → HCID 58668696, compound

HRID 2356980Notes

Reaction equation

HRID 2356980 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([C:15](=[O:21])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([OH:21])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58668692HCID 58668692, compound

Product 1

HCID 58668696HCID 58668696, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-(3-Fluoro-benzenesulfonyl)-chroman-4-one (3.31 g, 10.81 mmol) in THF (100 ml) was added NaBH4 (0.49 g, 12.9 mmol) at 0° C. The mixture was stirred at 0° C. for 3 hours. The reaction mixture was partitioned between water and EtOAc. The EtOAc layer was washed with brine, dried with MgSO4, filtered and concentrated. The residue was purified with flash chromatography to give 2.0 g of 7-(3-Fluorobenzene-sulfonyl)-chroman-4-ol, as a white foam. MS: 599.2 (2M−OH)+.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe EtOAc layer was washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with flash chromatography

Sources & evidence

ORD record
ord-7e0e9e2d5a7f40799ea8868797393f58
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

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