Borane → 2-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol

HRID 2056721Notes

Reaction equation

HRID 2056721 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][C:12](O)=[O:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:15]=1.B.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 6331BoraneHCID 10340Sodium CarbonateHCID 106357992-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)acetic acid

Product 1

HCID 536878432-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-((1S)-6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)acetic acid (21.3 g, 78.6 mmol) in anhydrous THF (65 mL) under an atmosphere of nitrogen and cooled to 0° C., was added dropwise borane.THF complex in THF (1M) (94 mL, 94 mmol). After stirring for 1 h between 0 and 10° C., the reaction mixture was treated with aqueous sodium carbonate then extracted into toluene. The organic layer was washed with dilute aqueous hydrochloric acid, then concentrated in vacuo to give the title compound as a white solid.

Workup

  1. extractionthen extracted into toluene
  2. washThe organic layer was washed with dilute aqueous hydrochloric acid
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c2052c3b95db415d840ea13208e9a876
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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