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

HRID 420191ノート

反応式

HRID 420191 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 962Water溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-863e6e400cfb45288fcbc416e42a0d4d
出典データセット
uspto-grants-2012_01
特許番号
US08093424B2

反応ノート

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