Benzene → (6-Benzenesulfonyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester

HRID 420191노트

반응식

HRID 420191 반응식
C1C=CC=CC=1.[C:7]1([S:13]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[C:22](=[O:26])[CH2:21][CH2:20][CH2:19]3)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH:28](C)[C:29]([O:31][CH2:32]C)=[O:30]>O.[Zn]>[CH3:32][O:31][C:29](=[O:30])[CH2:28][C:22]1([OH:26])[C:23]2[C:18](=[CH:17][C:16]([S:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)(=[O:15])=[O:14])=[CH:25][CH:24]=2)[CH2:19][CH2:20][CH2:21]1

참가 물질

6

반응물 3

HCID 241BenzeneHCID 79040Ethyl 2-bromopropionateHCID 590217396-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one

생성물 1

HCID 66651224(6-Benzenesulfonyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 962Water용매

실험 절차

A solution/suspension of anhydrous benzene (25 mL), powdered Zinc metal (0.505 g, 7.72 mmol), 12 (0.01 g) and 6-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one was stirred for 10 minutes at room temperature. Ethyl bromopropionate (0.784 mL, 1.18 g, 7.07 mmol) was added and the reaction mixture was heated to reflux for 2.5 hours. The reaction mixture was allowed to cool, diluted with 300 mL of water and extracted twice with 250 mL of EtOAc. The combined organic layers were washed with water and saturated brine, dried (MgSO4) and evaporated under reduced pressure to yield (6-benzenesulfonyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester. MS: 375 (M+H)+.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. temperatureto cool
  4. extractionextracted twice with 250 mL of EtOAc
  5. washThe combined organic layers were washed with water and saturated brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-863e6e400cfb45288fcbc416e42a0d4d
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093424B2

반응 노트

불러오는 중…