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

HRID 1766909Notes

Reaction equation

HRID 1766909 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:11]=1[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=NN=N1.[CH2:25]([O:28][P:29]([O:37][CH2:38][CH:39]=[CH2:40])N(C(C)C)C(C)C)[CH:26]=[CH2:27].C([O:45]O)(C)(C)C>>[P:29]([O:13][CH2:12][C:11]1[C:14]([O:18][CH3:19])=[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:28][CH2:25][CH:26]=[CH2:27])([O:37][CH2:38][CH:39]=[CH2:40])=[O:45]

Participants

5

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 4686855Diallyl diisopropylphosphoramiditeHCID 468330582-[(tert-Butyldimethylsilyl)oxymethyl]-6-methoxybenzyl alcoholHCID 178418441HCID 178418441, compound

Product 1

HCID 21110493Diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methoxybenzyl phosphateYield 60.4%

Procedure

According to a similar procedure to that described in Example 1-(10), 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methoxybenzyl alcohol (1.13 g, 4.00 mmol) obtained from Example 21-(2), tetrazole (672.3 mg, 9.6 mmol), bis(allyloxy)(diisopropylamino)phosphine (described in Tetrahedron Lett., 30, 4219 (1989); 1.37 g, 5.6 mmol), and tert-butyl hydroperoxide (80% di-tert-butyl peroxide solution; Merck; 0.9 g, 8 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 (60 g) column (eluent; ethyl acetate:hexane=1:6˜1:2) to give the title compound (1.07 g, 60% yield) as a colorless oil.

Workup

  1. customto afford
  2. extractionafter extraction

Sources & evidence

ORD record
ord-74fca1be25a44137aa392ac7013df7b0
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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