4-Hydroxy-1,7-bis(tert-butyldiphenylsilyloxy)heptane → 1,7-Bis(tert-butyldiphenylsilyloxy)heptan-4-one

HRID 222566Notes

Reaction equation

HRID 222566 reaction equation
[OH:1][CH:2]([CH2:24][CH2:25][CH2:26][O:27][Si:28]([C:41]([CH3:44])([CH3:43])[CH3:42])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:3][CH2:4][CH2:5][O:6][Si:7]([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl.CCOCC>[Si:7]([O:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH2:24][CH2:25][CH2:26][O:27][Si:28]([C:41]([CH3:44])([CH3:43])[CH3:42])([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:20]([CH3:21])([CH3:22])[CH3:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 689798234-Hydroxy-1,7-bis(tert-butyldiphenylsilyloxy)heptaneHCID 178418287HCID 178418287, compound

Product 1

HCID 689819261,7-Bis(tert-butyldiphenylsilyloxy)heptan-4-oneYield 71.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 49 (233 mg, 0.374 mmol) in CH2Cl2 (1 mL) was treated with PCC (121 mg, 0.561 mmol) at room temperature. Stirring was continued for 2 h. The mixture was diluted with Et2O, and the mixture was applied onto a plug of silica. The solid was washed with Et2O. The sample was concentrated, and the oily residue was chromatographed [silica, hexanes/ethyl acetate (10:1) to yield a colorless oil (166 mg, 71%): 1H NMR δ 1.82-1.88 (m, 4H), 2.55-2.58 (m, 4H), 3.65-3.72 (m, 4H), 7.43-7.45 (m, 12), 7.69-7.71 (m, 8H).

Workup

  1. washThe solid was washed with Et2O
  2. concentrationThe sample was concentrated
  3. customthe oily residue was chromatographed [silica, hexanes/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-4b642c89b19449d488e74a9df4d2a551
Source dataset
uspto-grants-2012_06
Patent number
US08207329B2

Reaction notes

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