Trityl chloride → HCID 18992038, compound

HRID 375740Notes

Reaction equation

HRID 375740 reaction equation
[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[C:10](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH3:8][C:3]([CH3:9])([CH2:2][O:1][C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 18992038HCID 18992038, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 25.0 g of methyl 3-hydroxy-2,2-dimethylpropanoate in 100 ml of pyridine, cooled to 0° C., were added 55.7 g of trityl chloride. The mixture was stirred at room temperature for 20 hours, and then the solvent was evaporated in vacuo. The residue was taken up in 200 ml of ethyl acetate, and the solution was washed successively with water, 1N hydrochloric acid, water, saturated sodium bicarbonate solution and brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated in vacuo. The residual oil was taken up in 50 ml of methylene chloride, and to the solution were added slowly, at 0° C., 300 ml of hexane. Trityl alcohol crystallized and was filtered off. The filtrate was evaporated in vacuo to yield 53.5 g of raw methyl 2,2-dimethyl-3-trityloxy-propionate.

Workup

  1. customthe solvent was evaporated in vacuo
  2. washthe solution was washed successively with water, 1N hydrochloric acid, water, saturated sodium bicarbonate solution and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated in vacuo
  5. additionto the solution were added slowly, at 0° C.
  6. customTrityl alcohol crystallized
  7. filtrationwas filtered off
  8. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c4580405572c4c96b5fb597d68f42631
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

Loading…