tert-Butyl hydroperoxide → Diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methylbenzyl phosphate

HRID 1766916Notes

Reaction equation

HRID 1766916 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:11]=1[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=NN=N1.[CH2:24]([O:27][P:28]([O:36][CH2:37][CH:38]=[CH2:39])N(C(C)C)C(C)C)[CH:25]=[CH2:26].C([O:44]O)(C)(C)C>>[P:28]([O:13][CH2:12][C:11]1[C:14]([CH3:18])=[CH:15][CH:16]=[CH:17][C:10]=1[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])([O:27][CH2:24][CH:25]=[CH2:26])([O:36][CH2:37][CH:38]=[CH2:39])=[O:44]

Participants

5

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 4686855Diallyl diisopropylphosphoramiditeHCID 211104532-[(Tert-butyldimethylsilyl)oxymethyl]-6-methylbenzylalcoholHCID 178418441HCID 178418441, compound

Product 1

HCID 21110494Diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methylbenzyl phosphateYield 88.4%

Procedure

According to a similar procedure to that described in Example 1-(10), 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methylbenzylalcohol (4.92 g, 18.5 mmol) obtained from Example 22-(2), tetrazole (3.23 g, 46.2 mmol), bis(allyloxy)(diisopropylamino)phosphine (described in Tetrahedron Lett., 30, 4219 (1989); 5.43 g, 22.2 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 (200 g) column (eluent; ethyl acetate:hexane=1:4˜2:3) to afford the title compound (6.03 g, 74% yield) as a colorless oil.

Workup

  1. customto afford
  2. extractionafter extraction

Sources & evidence

ORD record
ord-76e9d0215e2741908b8bc7d15b169001
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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