Boron Trichloride → HCID 18614297, compound

HRID 2268121Notes

Reaction equation

HRID 2268121 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:10][C:9]2[C:4](=[C:5]([O:13]C)[CH:6]=[CH:7][C:8]=2[O:11][CH3:12])[C:3]1=[O:15].B(Cl)(Cl)Cl>ClCCl>[CH3:1][C:2]1([CH3:16])[CH2:10][C:9]2[C:4](=[C:5]([OH:13])[CH:6]=[CH:7][C:8]=2[O:11][CH3:12])[C:3]1=[O:15]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 18614118HCID 18614118, compound

Product 1

HCID 18614297HCID 18614297, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.), stirred solution of 2,2-dimethyl-4,7-dimethoxy-indan-1-one (1 g) in dichloromethane (20 mL) was added boron trichloride (9 mL of a 1M solution in dichloromethane) over a 5 min period. The reaction was allowed to warm to RT, stirred for 3 h, then recooled to −78° C., quenched with ice, allowed to warm to RT and stirred for 1 h. The reaction was extracted with dichloromethane, the organic layers dried over sodium sulfate, concentrated in vacuo and flash chromatographed to afford 2,2-dimethyl-7-hydroxy-4-methoxyindan-1-one (0.85 g) as a tan oil.

Workup

  1. temperatureto warm to RT
  2. customrecooled to −78° C.
  3. customquenched with ice
  4. temperatureto warm to RT
  5. stirringstirred for 1 h
  6. extractionThe reaction was extracted with dichloromethane
  7. dry with materialthe organic layers dried over sodium sulfate
  8. concentrationconcentrated in vacuo and flash
  9. customchromatographed

Sources & evidence

ORD record
ord-911805a461984eeea0e8cfd62ba3ffcb
Source dataset
uspto-grants-2001_12
Patent number
US06326398B1

Reaction notes

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