Water → HCID 58988501, compound

HRID 1988869Notes

Reaction equation

HRID 1988869 reaction equation
[OH:1][C:2]([CH3:14])([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1)=[O:4].N1C=CC=CC=1.Cl[C:22]([O:24][CH3:25])=[O:23].O>O1CCCC1>[CH3:25][O:24][C:22](=[O:23])[O:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[C:2]([OH:1])([CH3:14])[CH3:13])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 59127545HCID 59127545, compound

Product 1

HCID 58988501HCID 58988501, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under argon gas, 3.0 g (15.5 mmol) of 2-hydroxy-1-(4-hydroxymethyl-phenyl)-2-methyl-propan-1-one and 1.5 g (19 mmol) of pyridine in 50 ml of tetrahydrofuran are introduced into a 100 ml reaction flask. The pale-yellow solution is cooled to 0° C., and 1.6 g (17 mmol) of methyl chloroformate diluted with 5 ml of tetrahydrofuran are added dropwise between 0 and 2° C. over 45 minutes. A whitish-yellow suspension is formed, which is further stirred overnight in an ice bath. After warming up to room temperature, the reaction mixture is poured into 50 ml of water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated. The crude product is purified by means of flash chromatography on silica gel (eluant: mixed hexanes:ethyl acetate 2:1). 2.3 g of carbonic acid 4-(2-hydroxy-2-methyl-propionyl)-benzyl ester methyl ester are obtained as a pale-yellow liquid. The structure is confirmed using a 1H NMR spectrum.

Workup

  1. additionare added dropwise between 0 and 2° C. over 45 minutes
  2. customA whitish-yellow suspension is formed
  3. temperatureAfter warming up to room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by means of flash chromatography on silica gel (eluant: mixed hexanes:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-1fea529a31cf4450930bc98189b14f92
Source dataset
uspto-grants-2010_01
Patent number
US07642296B2

Reaction notes

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