Trityl chloride → HCID 10698078, compound

HRID 1501900Notes

Reaction equation

HRID 1501900 reaction equation
[CH2:1]([O:17][CH2:18][C@H:19]([CH2:21][OH:22])[OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:23]1([C:29]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)Cl)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C1COCC1.C(#N)C.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:17][CH2:18][C@H:19]([CH2:21][O:22][C:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

8

Reactant 3

HCID 6456Trityl chlorideHCID 8471Triethylamine2×HCID 10448487(S)-3-(Hexadecyloxy)propane-1,2-diol

Product 1

HCID 10698078HCID 10698078, compoundYield 58.2%

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

18.47 grams of (S)-1-hexadecyl-sn-glycerol and 19 grams of triphenylchloromethane were dissolved in a mixture of 250 ml dry THF and 58 ml dry acetonitrile. 17 ml of triethylamine was added and the reaction mixture was refluxed for 17 hours. The reaction mixture was cooled to room temperature, poured on ice (20 grams) and triethylamine (5 ml), transferred to a separatory funnel and extracted with diethyl ether. The organic phase was washed consecutively with 200 ml water, twice with 200 ml dilute (1.5%) sulfuric acid, 200 ml water, 200 ml saturated aqueous sodium bicarbonate, and again with 200 ml water. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 41.79 grams of crude product as a residue. This residue was dissolved in 300 ml ethyl acetate and cooled at −20° C. overnight. The mixture was centrifuged (3,500 rotations per minute) at −10° C., and the mother liquid was poured of. The obtained solid melted and was dissolved in hexane and refrigerated (5±3° C.) overnight. Filtration of the precipitate yielded 18.97 grams of pure (R)-1-hexadecyl-3-trityl-sn-glycerol as an off-white solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 17 hours
  2. customtransferred to a separatory funnel
  3. extractionextracted with diethyl ether
  4. washThe organic phase was washed consecutively with 200 ml water, twice with 200 ml
  5. additiondilute (1.5%) sulfuric acid, 200 ml water, 200 ml saturated aqueous sodium bicarbonate
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customto yield 41.79 grams of crude product as a residue
  9. temperaturecooled at −20° C. overnight
  10. customat −10° C.
  11. additionthe mother liquid was poured of
  12. customrefrigerated (5±3° C.) overnight
  13. filtrationFiltration of the precipitate

Sources & evidence

ORD record
ord-e634577fc2c84d209ff9e6cb982f629f
Source dataset
uspto-grants-2015_12
Patent number
US09206206B2

Reaction notes

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