HCID 21884690, compound → HCID 21884696, compound

HRID 722401Notes

Reaction equation

HRID 722401 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:30])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:14]=2)=[CH:7][CH:6]=1>ClCCl>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:30])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][Si:20]([CH:24]([CH3:26])[CH3:25])([CH:27]([CH3:29])[CH3:28])[CH:21]([CH3:23])[CH3:22])[CH:14]=2)=[CH:7][CH:6]=1

Participants

3

Reactant 1

HCID 21884690HCID 21884690, compound

Product 1

HCID 21884696HCID 21884696, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 40.7 g (0.095 mol) of 4′-methoxymethyloxy-2-(3-triisopropylsilyloxy-phenyl)-acetophenone (5c), from Example 5, in 400 mL of dichloromethane at 0° C. was added all at once 37.5 g (0.099 mol) of solid trimethylammoniumphenyl perbromide. The ice-water bath was removed and the reaction mixture was stirred further for 4 h under an inert atmosphere of nitrogen. The reaction mixture was partitioned between ethyl acetate, ice, brine, 5% aqueous sodium thiosulfate, and saturated sodium bicarbonate. The organic phase was separated washed with brine; dried over anhydrous sodium sulfate, filtered, evaporated, and dried in vacuo to give the crude product which was used without further purification. 1H 500 MHz NMR(CDCl3) ppm(δ): 1.07 (d, 18H), 1.2 (m, 3H), and 6.3 (s, 1H).

Workup

  1. customThe ice-water bath was removed
  2. customThe reaction mixture was partitioned between ethyl acetate, ice, brine, 5% aqueous sodium thiosulfate, and saturated sodium bicarbonate
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-e74e431538c44fe3bcc0b6f48001aecb
Source dataset
uspto-grants-2006_11
Patent number
US07138426B2

Reaction notes

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