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Water → 3-(2-Methylsulfonylvinyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde

HRID 1836916
ノート
印刷プレビュー

反応式

HRID 1836916 の反応式
Br[C:2]1[C:3]([CH:16]=[O:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[CH:18]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH2:19].C(N(CC)CC)C.O>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:23][S:20]([CH:18]=[CH:19][C:2]1[C:3]([CH:16]=[O:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1)(=[O:22])=[O:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 19354Methyl vinyl sulfoneHCID 177898873-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

生成物 1

HCID 598987073-(2-Methylsulfonylvinyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde収率 62%

試薬・触媒・溶媒 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 6228Dimethylformamide溶媒

実験手順

A solution of 0.537 g (1.82 mmol) of 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde, 0.579 g (5.46 mmol) of methyl vinyl sulfone, 0.191 g (0.27 mmol) of tetrakis(triphenylphosphine) palladium and 5.23 g (51.7 mmol) of triethylamine in 12 ml dimethylformamide was heated to 100° C. under argon for 5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude material was purified by flash chromatography (elution with 25% ethyl acetate/hexane) to afford 0.359 g (62%) of 3-(2-methylsulfonylvinyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde (M+1=321).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (elution with 25% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-386d2237ac3c4cd29271bbfcd147c517
出典データセット
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06777418B2

反応ノート

読み込み中…

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