Ethyl Acetate → HCID 53665350, compound

HRID 1725320Notes

Reaction equation

HRID 1725320 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:17]=[CH:16][C:15]([S:18][CH2:19][CH2:20][OH:21])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.C(N([CH:28]([CH3:30])[CH3:29])CC)(C)C.[C:31](Cl)(=[O:34])[CH:32]=[CH2:33].C(OCC)(=[O:38])C>>[C:31]([O:21][CH2:20][CH2:19][S:18][C:15]1[CH:16]=[CH:17][C:12]([S:11][C:8]2[CH:7]=[CH:6][C:5]([S:4][CH2:3][CH2:2][O:1][C:30](=[O:38])[CH:28]=[CH2:29])=[CH:10][CH:9]=2)=[CH:13][CH:14]=1)(=[O:34])[CH:32]=[CH2:33]

Participants

5

Reactant 4

HCID 8857Ethyl AcetateHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 11515600HCID 11515600, compound

Product 1

HCID 53665350HCID 53665350, compound

Conditions

Temperature
5 °C

Procedure

A solution containing 13 grams of (7) and 14.9 grams of diisopropylethylamine was cooled to 5° C., and to it was added 10.4 grams of acryloyl chloride over a period of 20 minutes. The mixture was stirred at 5-10° C. for two hours after which it was poured into a mixture containing 75 ml of 1N HCL and 100 ml of ethyl acetate. After stirring for five minutes the organic phase was removed and washed with saturated KCl solution followed by 10 percent aqueous potassium bicarbonate. The solvent was removed and the residue purified on column chromatography (silica gel eluted with 25% ethylacetate/hexane) to yield in the first fraction 8.5 grams of (8).

Workup

  1. additionwas poured into a mixture
  2. stirringAfter stirring for five minutes the organic phase
  3. customwas removed
  4. washwashed with saturated KCl solution
  5. customThe solvent was removed
  6. customthe residue purified on column chromatography (silica gel eluted with 25% ethylacetate/hexane)

Sources & evidence

ORD record
ord-eb4edd6a6fa64ba0b3899d0d569363bd
Source dataset
uspto-grants-2009_02
Patent number
US07491441B2

Reaction notes

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