Tempo → 1-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]acetaldehyde

HRID 1820294Notes

Reaction equation

HRID 1820294 reaction equation
CC1(C)N([O])C(C)(C)CCC1.[O:12]([CH2:30][CH2:31][C:32]1(CCO)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:41](O)(=[O:43])[CH3:42].C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[O:12]([CH2:30][CH2:31][C:32]1([C:41](=[O:43])[CH3:42])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[Si:13]([C:26]([CH3:28])([CH3:27])[CH3:29])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 2724126TempoHCID 12217721Iodo benzene diacetateHCID 574278602-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethanol

Product 1

HCID 231098901-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]acetaldehydeYield 160.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (31 mg, 0.20 mmol) to a solution of 2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethanol (810 mg, 1.97 mmol) and iodobenzene diacetate (700 mg, 2.17 mmol) in methylene chloride (10 mL), the mixture was stirred at room temperature for 4 hours. The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine in that order and dried (anhydrous sodium sulfate), and then the solvent was distilled off under reduced pressure to obtain the title compound as a brown oil (1.29 g). This was used without purification for the following step.

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine in that order
  2. dry with materialdried (anhydrous sodium sulfate)
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e72eb954a3f44f64b8ee325944ed2115
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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