Borane;tetrahydrofuran → HCID 28293918, compound

HRID 2177039Notes

Reaction equation

HRID 2177039 reaction equation
B.O1CCCC1.[Cl:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][CH2:13][C:14]2=[O:17])=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.O1CCCC1>[Cl:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][CH2:13][C@H:14]2[OH:17])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 51007056-Chloro-1-indanone

Product 1

HCID 28293918HCID 28293918, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of borane-tetrahydrofuran (1.8 mL, 1.8 mmol, Aldrich, 1 M solution in THF) and (S)-MeCBS (0.3 mL, 0.3 mmol, Aldrich, 1 M solution in toluene) was added a solution of 6-chloro-1-indanone (0.5 g, 3.0 mmol) in anhydrous tetrahydrofuran slowly over 30 min at room temperature. After complete addition, the reaction mixture was stirred for 10 min, quenched with 2N hydrochloric acid over 30 min. The reaction mixture was extracted with ether, dried, filtered and concentrated to afford 500 mg of (R)-6-chloroindan-1-ol.

Workup

  1. additionAfter complete addition
  2. customquenched with 2N hydrochloric acid over 30 min
  3. extractionThe reaction mixture was extracted with ether
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-01b672682c7f461eb0ca01c25ab13b2c
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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