tert-Butyl hydroperoxide → HCID 46834796, compound

HRID 1766941Notes

Reaction equation

HRID 1766941 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([CH2:15][OH:16])=[CH:12][O:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=NN=N1.[CH2:22]([O:25][P:26]([O:34][CH2:35][CH:36]=[CH2:37])N(C(C)C)C(C)C)[CH:23]=[CH2:24].C([O:42]O)(C)(C)C>ClCCl.CCCCCC.C(OCC)(=O)C>[P:26]([O:16][CH2:15][C:11]1[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:14][O:13][CH:12]=1)([O:25][CH2:22][CH:23]=[CH2:24])([O:34][CH2:35][CH:36]=[CH2:37])=[O:42]

Participants

8

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 4686855Diallyl diisopropylphosphoramiditeHCID 21110474HCID 21110474, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 46834796HCID 46834796, compoundYield 94.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

[4-[(tert-Butyldimethylsilyl)oxymethyl]-3-furyl]methanol (174 mg, 0.72 mmol) obtained from Example 35-(1) was reacted in dichloromethane (3 ml) with tetrazole (61 mg, 0.87 mmol), bis(allyloxy)(diisopropylamino)phosphine (265 mg, 1.08 mmol), and tert-butyl hydroperoxide (80% di-tert-butyl peroxide solution; Merck; 135 mg, 1.2 mmol) according to a similar procedure to that described in Example 1-(10). The oily residue obtained by extraction was subjected to chromatography on a silica gel (5 g) column (eluent; ethyl acetate:hexane=1:4) to afford the title compound (273 mg, 93% yield) as a colorless oil.

Workup

  1. customThe oily residue obtained by extraction

Sources & evidence

ORD record
ord-009001cf6af64ea0a22e0e8d1d81d995
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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