HCID 131730695, compound → HCID 131730694, compound

HRID 446648Notes

Reaction equation

HRID 446648 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].O[C:6]([C:9]1[CH:14]=[C:13]([CH:15]([C:20]([CH3:23])([CH3:22])[CH3:21])[O:16][SiH:17]([CH3:19])[CH3:18])[CH:12]=[C:11]([CH:24](C(C)(C)C)[O:25][SiH](C)C)[CH:10]=1)([CH3:8])[CH3:7]>ClCCCl.[I-].[Zn+2].[I-]>[C:1]([O:4][C:6]([C:9]1[CH:10]=[C:11]([CH2:24][OH:25])[CH:12]=[C:13]([CH:15]([C:20]([CH3:22])([CH3:21])[CH3:23])[O:16][SiH:17]([CH3:19])[CH3:18])[CH:14]=1)([CH3:8])[CH3:7])(=[S:3])[CH3:2]

Participants

5

Reactant 2

HCID 131730695HCID 131730695, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 131730694HCID 131730694, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

404 μl of thioacetic acid and 376 mg of zinc iodide are added to 1 g of 1-(1-hydroxy-1-methylethyl)-3,5-bis[(tert-butyl)dimethylsilanyloxymethyl]benzene in solution in 4.7 ml of 1,2-dichloroethane. The mixture is heated at 50° C. for 40 min. After returning to AT, the salts are removed by filtration, the organic phase is concentrated under RP and the residue is purified by flash chromatography on silica (Biotage 40+M) using a gradient from 0 to 30% AcOEt in heptane. 248 mg of 1-[3-[(tert-butyl)dimethylsilanyloxymethyl]-5-(hydroxymethyl)phenyl]-1-methylethyl thioacetate are thus obtained.

Workup

  1. customthe salts are removed by filtration
  2. concentrationthe organic phase is concentrated under RP
  3. customthe residue is purified by flash chromatography on silica (Biotage 40+M)

Sources & evidence

ORD record
ord-c069035542fc432ead181de66be6f626
Source dataset
uspto-grants-2013_07
Patent number
US08481042B2

Reaction notes

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