Trityl chloride → (S)-4-benzyloxy-1-trityloxy-2-butanol

HRID 1168049Notes

Reaction equation

HRID 1168049 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([OH:14])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([OH:14])[CH2:12][O:13][C:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 9794180(S)-4-Benzyloxy-1,2-butanediol

Product 1

HCID 11015650(S)-4-benzyloxy-1-trityloxy-2-butanolYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In toluene (100 ml) were dissolved (S)-4-benzyloxy-1,2-butanediol (25.8 g, 0.132 mol), triethylamine (20.2 ml, 0.145 mol) and 4-N,N-dimethylaminopyridine (DMAP) (0.80 g, 6.58 mmol). After cooling in ice bath, trityl chloride (36.69 g, 0.1316 mol) was added to the solution and the mixture was stirred at room temperature for 10 hours. The mixture was condensed in vacuo, diluted with ethyl acetate, washed with water and then saturated brine, dried on sodium sulfate, filtered and condensed in vacuo to give (S)-4-benzyloxy-1-trityloxy-2-butanol quantitatively (55.89, yield 100%).

Workup

  1. temperatureAfter cooling in ice bath
  2. customcondensed in vacuo
  3. washwashed with water
  4. dry with materialsaturated brine, dried on sodium sulfate
  5. filtrationfiltered
  6. customcondensed in vacuo

Sources & evidence

ORD record
ord-f1587c997a9841998fb1cbfc8baf52ff
Source dataset
uspto-grants-2003_09
Patent number
US06620977B1

Reaction notes

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