Methanol → HCID 58136741, compound

HRID 877164Notes

Reaction equation

HRID 877164 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][C:10]([CH3:21])([C:16]([O:18][CH2:19]C)=[O:17])[CH2:11]2.CO.O>ClCCl>[OH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][C:10]([CH3:21])([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 11276376HCID 11276376, compound

Product 1

HCID 58136741HCID 58136741, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

At 0° C., 15.2 ml (15.24 mmol) of a 1 M solution of boron tribromide in dichloromethane were added to a solution of 1.19 g (5.08 mmol) of ethyl 4-methoxy-2-methyl-2,3-dihydro-1H-indene-2-carboxylate in 20 ml of dichloromethane. Stirring at 0° C. was continued for one hour. 16 ml of methanol were then added, and the reaction mixture was stirred overnight. 10 ml of water and 10 ml of dichloromethane were then added. After phase separation, the aqueous phase was extracted three times with dichloromethane and the combined organic phases were dried over magnesium sulfate. After filtration, the solvent was evaporated to dryness under reduced pressure. This gave 897 mg (4.35 mmol, 86% of theory) of a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customAfter phase separation
  3. extractionthe aqueous phase was extracted three times with dichloromethane
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7f4caa3e59a94b898da9feb6fa553b87
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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