Methanesulfonic Acid → HCID 18614155, compound

HRID 1265157Notes

Reaction equation

HRID 1265157 reaction equation
[CH3:1][C:2]1([CH3:15])[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.CS(O)(=O)=O.C([SiH](CC)CC)C>ClCCl>[CH3:1][C:2]1([CH3:15])[CH2:10][C:9]2[C:4](=[C:5]([OH:13])[CH:6]=[CH:7][C:8]=2[O:11][CH3:12])[CH2:3]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic Acid2×HCID 12052Triethylsilane2×HCID 18614297HCID 18614297, compound

Product 1

HCID 18614155HCID 18614155, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,2-dimethyl-7-hydroxy-4-methoxyindan-1-one (500 mg) and methanesulfonic acid (466 mg) in dichloromethane (12 mL) was added triethylsilane (564 mg). Every 0.5 h, over a 3 h period, additional portions of methanesulfonic acid and triethylsilane were added. The reaction was partitioned between water and dichloromethane, the organic layer dried over sodium sulfate, concentrated in vacuo and the resulting oil flash chromatographed (1:1, chloroform:hexanes) to afford 2,2-dimethyl-7-hydroxy-4-methoxyindane (230 mg) as a colorless waxy solid.

Workup

  1. customThe reaction was partitioned between water and dichloromethane
  2. dry with materialthe organic layer dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe resulting oil flash chromatographed (1:1, chloroform:hexanes)

Sources & evidence

ORD record
ord-115b1613fa324506ac065db23e2ce2fc
Source dataset
uspto-grants-2003_04
Patent number
US06545018B2

Reaction notes

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