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Toluene → Methyl 2-methyl-2-mesyloxymethyl-3-(4-chlorophenyl)-3-keto-propanoate

HRID 1607214
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HRID 1607214 반응식
[CH3:1][C:2]([CH2:16][OH:17])([C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8])[C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.C1(C)C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl.O>[CH3:1][C:2]([CH2:16][O:17][S:33]([CH3:32])(=[O:35])=[O:34])([C:7]([C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:8])[C:3]([O:5][CH3:6])=[O:4]
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참가 물질

7

반응물 4

HCID 1140TolueneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19852106Methyl 2-methyl-2-hydroxymethyl-3-(4-chlorophenyl)-3-keto-propanoate

생성물 1

HCID 19852270Methyl 2-methyl-2-mesyloxymethyl-3-(4-chlorophenyl)-3-keto-propanoate수율 74%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6344Dichloromethane용매

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온도
-10 °C

실험 절차

Into a 5 liter RBF is placed 100 g (4.37 mole) of methyl 2-methyl-2-hydroxymethyl-3-(4-chlorophenyl)-3-keto-propanoate, 473 g (4.25 mole) of triethylamine, and 2 liters of toluene. This mixture is cooled to -10° C. and methane sulfonyl chloride, 488 g (4.25 mole), is added over 30 minutes. The internal temperature rose to 40° C. by the end of the addition. After stirring at room temperature for 2 hours, the mixture is worked up with 4 liters of cold water and 1 liter methylene chloride. The resulting red semisolid (1400 g) is crystalized using 200 ml of hot ethyl acetate and adding 1500 ml of hexane. Yielding 1060 g (74%) of a light yellow solid mp 85°-86° C., methyl 2-methyl-2-mesyloxymethyl-3-(4-chlorophenyl)-3-keto-propanoate. NMR data was consistent with the structure.

후처리

  1. additionThe internal temperature rose to 40° C. by the end of the addition
  2. customThe resulting red semisolid (1400 g) is crystalized
  3. additionadding 1500 ml of hexane

출처 및 근거

ORD 기록
ord-103cee6d9c124303ae5524bc607ef47a
출처 데이터셋
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04863947

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