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Water → 8-benzyloxy-5-(2-chloro-1-hydroxy-ethyl)-1H-quinolin-2-one

HRID 969455
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HRID 969455 반응식
[BH4-].[Li+].[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:22](=[O:25])[CH2:23][Cl:24])=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[CH:17]=[CH:16]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.ClCCl.O>C1COCC1>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:22]([OH:25])[CH2:23][Cl:24])=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[CH:17]=[CH:16]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 6344DichloromethaneHCID 4148881Lithium borohydrideHCID 109035505-(2-chloroacetyl)-8-phenylmethoxy-1H-quinolin-2-one

생성물 1

HCID 224992458-benzyloxy-5-(2-chloro-1-hydroxy-ethyl)-1H-quinolin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매
2회

반응 조건

온도
0 °C

실험 절차

238 mL of a 2 molar solution of lithium borohydride in THF are added dropwise to 52 g (159 mmol) 8-benzyloxy-5-(2-chloro-acetyl)-1H-quinolin-2-one in 650 mL THF at 0° C. It is stirred for two hours at 0° C., then heated to ambient temperature, combined with 200 mL dichloromethane and 75 mL water and stirred for a further hour. The precipitated solid is suction filtered and the organic phase of the filtrate is separated off and freed from the solvent. The residue is combined with the solid from the preceding filtration and repeatedly stirred with diethyl ether and THF. Yield: 51.6 g (99%); mass spectroscopy [M+H]+=330/32.

후처리

  1. temperatureheated to ambient temperature
  2. stirringstirred for a further hour
  3. filtrationfiltered
  4. customthe organic phase of the filtrate is separated off
  5. filtrationThe residue is combined with the solid from the preceding filtration
  6. stirringrepeatedly stirred with diethyl ether and THF

출처 및 근거

ORD 기록
ord-88314aa98dbd4c2088823ca21dc1d30d
출처 데이터셋
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07307076B2

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