Formic Acid → (S)-4-broMo-2,3-dihydro-1H-inden-1-ol

HRID 1515115Notes

Reaction equation

HRID 1515115 reaction equation
C(O)=O.C(N(CC)CC)C.ClCCl.[Br:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][CH2:18][C:19]2=[O:24]>O>[Br:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][CH2:18][C@@H:19]2[OH:24]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 6344DichloromethaneHCID 8471TriethylamineHCID 987131-Indanone, 4-bromo-

Product 1

HCID 51915874(S)-4-broMo-2,3-dihydro-1H-inden-1-olYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of formic acid (1.20 mL, 31.5 mmol) and triethylamine (3.76 mL, 27.0 mmol), a dichloromethane (6.0 mL) solution of 4-bromoindan-1-one (1.90 g, 9.00 mmol) was added, and chloro[(1S,2S)—N-(p-toluenesulfonyl)-1,2-diphenyl ethanediamine](mesitylene)ruthenium(II) (168 mg, 0.270 mmol) was added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. Water was added to the reaction solution, and the organic matter was extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution and a saturated sodium chloride solution, then dried over anhydrous sodium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 65:35 (v/v)), whereby the objective title compound was obtained as a white solid (1.90 g, yield: 99%).

Workup

  1. extractionthe organic matter was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium bicarbonate solution
  3. dry with materiala saturated sodium chloride solution, then dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  6. customwas obtained
  7. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 65:35 (v/v)), whereby the objective title compound

Sources & evidence

ORD record
ord-8d7b1ea82feb496ea078afa93c75b447
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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