Silanol, trimethyl-, 1,1'-sulfate → HCID 18767021, compound

HRID 481265Notes

Reaction equation

HRID 481265 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH:20]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][O:51]C1CCCCO1)[CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33]C1CCCCO1.C[Si](OS(O[Si](C)(C)C)(=O)=O)(C)C>CO>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH:20]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][OH:51])[CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33]

Participants

4

Reactant 2

HCID 87573Silanol, trimethyl-, 1,1'-sulfateHCID 187670141,2,3-Tris(10-[tetrahydropyranyloxy]decyloxy)propane

Product 1

HCID 18767021HCID 18767021, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 13 g 1,2,3-tris(10-[tetrahydropyranyloxy]decyloxy)propane, 1 g bis(trimethylsilyl)sulphate and 250 ml methanol is stirred at room temperature for 2 hours. The reaction mixture is evaporated down. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1/1 v/v) as eluent and recrystallisation from acetonitrile to yield 7.1 g of 1,2,3-tris(10-hydroxydecyloxy)propane.

Workup

  1. customThe reaction mixture is evaporated down
  2. customThe residue is purified by column chromatography on silica gel
  3. customrecrystallisation from acetonitrile

Sources & evidence

ORD record
ord-94195f89aa6f498e8fa791ae8c2f9257
Source dataset
uspto-grants-2003_11
Patent number
US06653499B1

Reaction notes

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