Water → 2-[4-[2-(tert-Butyldiphenylsilyloxy)ethoxy]phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene

HRID 650021Notes

Reaction equation

HRID 650021 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9]=2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.Br[CH2:33][CH2:34][O:35][Si:36]([C:49]([CH3:52])([CH3:51])[CH3:50])([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Si:36]([O:35][CH2:34][CH2:33][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9]=2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)=[CH:20][CH:19]=2)=[CH:4][CH:3]=1)([C:49]([CH3:50])([CH3:51])[CH3:52])([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10915442(2-Bromoethoxy)(tert-butyl)diphenylsilaneHCID 224626554-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenol

Product 1

HCID 217063512-[4-[2-(tert-Butyldiphenylsilyloxy)ethoxy]phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiopheneYield 126.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2.00 g (4.66 mmol) of 2-(4-hydroxyphenyl)-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene, 1.86 g (5.12 mmol) of 1-bromo-2-(tert-butyldiphenyl-silyloxy)ethane, and 1.93 g (14.0 mmol) of K2CO3 in 50 mL DMF was heated to 50° C. for 22 h. The reaction was poured into 250 mL of H2O and the mixture extracted with EtOAc (3×100 mL). The combined organic extracts were washed with H2O (2×100 mL), dried over K2CO3, filtered and concentrated in vacuo to give 4.21 g of an oily solid. Purification by flash chromatography (SiO2; 0.1% then 0.2% then 0.5% MeOH in CHCl3 sat'd with NH4OH) afforded 2.76 g (3.88 mmol; 83%) of the title compound as an oil.

Workup

  1. extractionthe mixture extracted with EtOAc (3×100 mL)
  2. washThe combined organic extracts were washed with H2O (2×100 mL)
  3. dry with materialdried over K2CO3
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45202d8be5704a5cbb85e9a50ade17b3
Source dataset
uspto-grants-2001_08
Patent number
US06271227B1

Reaction notes

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