Acetonitrile → (S)-1-(Benzyloxy)-3-(trityloxy)propan-2-ol

HRID 1501898Notes

Reaction equation

HRID 1501898 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]1([C:20]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1COCC1.C(#N)C>C(N(CC)CC)C>[C:20]([O:12][CH2:11][C@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:13])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6456Trityl chlorideHCID 8028TetrahydrofuranHCID 2724795(R)-3-(benzyloxy)propane-1,2-diol

Product 1

HCID 11582634(S)-1-(Benzyloxy)-3-(trityloxy)propan-2-olYield 94.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

5 grams (27.44 mmol) of (R)-(+)-3-benzyloxy-1,2-propanediol and 10 grams (35.87 mmol) of triphenylchloromethane were added to 100 ml dry THF and 25 ml dry acetonitrile. 8 ml of dry triethylamine were added and the reaction mixture was refluxed for 17 hours. The reaction mixture was cooled to room temperature, poured on ice (100 grams), transferred to a separatory funnel and extracted thrice with 100 ml diethyl ether. The organic phase was washed consecutively with 100 ml water, twice with 100 ml dilute (1.5%) sulfuric acid, 100 ml water, 100 ml concentrated sodium bicarbonate solution, and again with 100 ml water. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure, yielding 11 grams of 1-trityl-3-benzyl-sn-glycerol as a yellow oil. The yield was 94%.

Workup

  1. temperaturethe reaction mixture was refluxed for 17 hours
  2. additionpoured on ice (100 grams)
  3. customtransferred to a separatory funnel
  4. extractionextracted thrice with 100 ml diethyl ether
  5. washThe organic phase was washed consecutively with 100 ml water, twice with 100 ml
  6. additiondilute (1.5%) sulfuric acid, 100 ml water, 100 ml concentrated sodium bicarbonate solution
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-95a3d8f9c6da441cb8d6df65dfb783e8
Source dataset
uspto-grants-2015_12
Patent number
US09206206B2

Reaction notes

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