Trityl chloride → HCID 14206220, compound

HRID 329505Notes

Reaction equation

HRID 329505 reaction equation
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]([O:28][C@H:29]([CH2:34][CH2:35][CH2:36][O:37][Si:38]([C:51]([CH3:54])([CH3:53])[CH3:52])([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:30]([OH:33])[CH2:31][OH:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.O>[CH2:21]([O:28][C@H:29]([CH2:34][CH2:35][CH2:36][O:37][Si:38]([C:51]([CH3:54])([CH3:53])[CH3:52])([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C@H:30]([OH:33])[CH2:31][O:32][C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 14206217HCID 14206217, compound

Product 1

HCID 14206220HCID 14206220, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

18.33 g of triphenylmethyl chloride were added to a solution of 26.22 g of (2R, 3R)-3-benzyloxy-6-(t-butyldiphenylsilyloxy)hexane-1,2-diol (prepared as described in Preparation 17) and 18.40 ml of triethylamine in 500 ml of toluene. The resulting mixture was heated under reflux for 3 hours. At the end of this time, it was cooled and then diluted with water. It was then extracted three times with ethyl acetate. The combined extracts were washed, in turn, with water, with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, after which they were dried over anhydrous magnesium sulfate, and the solvent was stripped off by evaporation under reduced pressure. The resulting oily residue was dissolved in 270 ml of tetrahydrofuran, and then 90 ml of a saturated aqueous solution of sodium bicarbonate were added, and the resulting mixture was stirred at room temperature for 1 hour. After this work-up, 40 g of the oily product were subjected to column chromatography through 500 g of silica gel, 37.01 g of the title compound were obtained, as a colorless oil, from those fractions eluted with mixtures of hexane and ethyl acetate ranging from 95:5 to 9:1 by volume.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAt the end of this time, it was cooled
  4. extractionIt was then extracted three times with ethyl acetate
  5. washThe combined extracts were washed, in turn, with water, with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride
  6. dry with materialafter which they were dried over anhydrous magnesium sulfate
  7. customthe solvent was stripped off by evaporation under reduced pressure
  8. dissolutionThe resulting oily residue was dissolved in 270 ml of tetrahydrofuran
  9. addition90 ml of a saturated aqueous solution of sodium bicarbonate were added

Sources & evidence

ORD record
ord-d26d7fb074444d078002c80b07dbd4b3
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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