tert-Butyl hydroperoxide → HCID 46834505, compound

HRID 1766921Notes

Reaction equation

HRID 1766921 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[C:18]([CH2:20][OH:21])=[CH:17][CH:16]=[CH:15]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=NN=N1.[CH2:27]([O:30][P:31]([O:39][CH2:40][CH:41]=[CH2:42])N(C(C)C)C(C)C)[CH:28]=[CH2:29].C([O:47]O)(C)(C)C>>[P:31]([O:21][CH2:20][C:18]1[C:19]2[C:14](=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:15]=[CH:16][CH:17]=1)([O:30][CH2:27][CH:28]=[CH2:29])([O:39][CH2:40][CH:41]=[CH2:42])=[O:47]

Participants

5

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 4686855Diallyl diisopropylphosphoramiditeHCID 15253504HCID 15253504, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 46834505HCID 46834505, compoundYield 81%

Procedure

According to a similar procedure to that described in Example 1-(10), [8-[(tert-butyldimethylsilyl)oxymethyl]-1-naphthyl]methanol (described in Aust. J. Chem., 49, 793 (1996); 4.04 g, 13.4 mmol), tetrazole (2.34 g, 33.4 mmol), bis(allyloxy)(diisopropylamino)phosphine (described in Tetrahedron Lett., 30, 4219 (1989); 3.93 g, 16.0 mmol), and tert-butyl hydroperoxide (80% di-tert-butyl peroxide solution; Merck; 1.8 g, 16 mmol) were reacted, and the reaction mixture was worked up to afford, after extraction, an oily residue. The residue was subjected to chromatography on a silica gel (120 g) column (eluent; ethyl acetate:hexane=1:5˜1:2) to afford the title compound (5.02 g, 81% yield) as a colorless oil.

Workup

  1. customto afford
  2. extractionafter extraction

Sources & evidence

ORD record
ord-7feebc360bea4bbdab8f1a82ed0301aa
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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