Chlorotrimethylsilane → HCID 67079154, compound

HRID 1047405Notes

Reaction equation

HRID 1047405 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[CH:9]([O:12][CH:13]([CH3:15])[CH3:14])[O:10][CH3:11].C([Li])CCC.[CH3:21][Si:22](Cl)([CH3:24])[CH3:23].[CH3:26][Si:27]([CH3:53])([CH3:52])[O:28][CH:29]1[CH:34]([O:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[CH:33]([O:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:32]([CH2:45][O:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[O:31][C:30]1=[O:51]>CCCCCC.C(N(CC)CC)C>[CH3:21][Si:22]([CH3:24])([CH3:23])[O:51][C:30]1([C:2]2[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=2[CH:9]([O:12][CH:13]([CH3:15])[CH3:14])[O:10][CH3:11])[CH:29]([O:28][Si:27]([CH3:26])([CH3:52])[CH3:53])[CH:34]([O:35][Si:36]([CH3:37])([CH3:38])[CH3:39])[CH:33]([O:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:32]([CH2:45][O:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[O:31]1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 523407HCID 523407, compoundHCID 67079339HCID 67079339, compoundHCID 178418339Butyllithium

Product 1

HCID 67079154HCID 67079154, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8471TriethylamineSolvent

Procedure

According to the procedure of Example 1, Step 3, 2,4-dibromo-1-(1-methoxy-1-methylethoxymethyl)benzene was treated with n-butyllithium in hexane, 3,4,5-tris(trimethylsilyloxy)-6-trimethylsilyloxymethyl-tetrahydropyran-2-one, triethylamine, and trimethylsilyl chloride. The reaction mixture was subjected to workup procedure, and the resulting residue was purified by HPLC (column; Inertsil ODS-3, 20 mm I.D.×250 mm; acetonitrile, 30 mL/min) to give the titled compound as two isolated diastereomers.

Workup

  1. customthe resulting residue was purified by HPLC (column; Inertsil ODS-3, 20 mm I.D.×250 mm; acetonitrile, 30 mL/min)

Sources & evidence

ORD record
ord-56506499ed5545ff9c36c891cafce693
Source dataset
uspto-grants-2013_10
Patent number
US08569520B2

Reaction notes

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