Trityl chloride → HCID 67528372, compound

HRID 1393888Notes

Reaction equation

HRID 1393888 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8][CH2:9][CH2:10][C@H:11]([OH:14])[CH2:12][OH:13])=[CH:5][CH:4]=1.[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:17]([O:13][CH2:12][C@@H:11]([OH:14])[CH2:10][CH2:9][O:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 11816988(S)-4-O-(4-methoxybenzyl)-1,2,4-butanetriol

Product 1

HCID 67528372HCID 67528372, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Compound 4 (22.6 grams, 100 mmoles) in 200 ml dry pyridine, trityl chloride (30.7 grams, 110 mmoles) was added dropwise, under argon atmosphere and the mixture was stirred overnight at room temperature. The solvent was thereafter evaporated to dryness and the residue was extracted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and the solvent was thereafter removed under reduced pressure. The resulting yellowish oily residue was purified by silica gel chromatography, using 1:2 (v:v) ethyl acetate:hexane as eluent. 41.2 grams (88% yield) of Compound 5 were obtained as an oil.

Workup

  1. customThe solvent was thereafter evaporated to dryness
  2. extractionthe residue was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was thereafter removed under reduced pressure
  6. customThe resulting yellowish oily residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f8ccf26ece8c48799448d3887fb7b66a
Source dataset
uspto-grants-2008_03
Patent number
US07348148B2

Reaction notes

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