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2,3-Dihydroxybutanedioic Acid → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzaldehyde

HRID 1382434
ノート
印刷プレビュー

反応式

HRID 1382434 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1([CH3:34])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16]([C:24]#[C:25][C:26]3[CH:33]=[CH:32][C:29]([C:30]#N)=[CH:28][CH:27]=3)[CH:15]=[CH:14][C:13]1=2.C(O)(=O)C(C(C(O)=O)O)[OH:37]>CCCCCC.CCOCC>[CH3:11][C:12]1([CH3:34])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16]([C:24]#[C:25][C:26]3[CH:33]=[CH:32][C:29]([CH:30]=[O:37])=[CH:28][CH:27]=3)[CH:15]=[CH:14][C:13]1=2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 136048264-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrileHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 197869634-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzaldehyde収率 38%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether
溶媒
HCID 8058Hexane溶媒

実験手順

56 ml (67 millimoles) of a 20% strength solution of diisobutylaluminum hydride in hexane were added to a solution of 10 g (32 millimoles) of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzonitrile (Example 1) in 120 ml of absolute ether. The mixture was stirred for a further 40 minutes, 150 ml of saturated tartaric acid solution were added dropwise and stirring was continued for a further hour. Thereafter, the mixture was extracted three times with ether and the combined ether phases were washed twice with water, dried over Na2SO4 and evaporated down. Recrystallization of the residue from isopropanol gave 3.6 g (38%) of the title compound of melting point 130° C.

後処理

  1. stirringstirring
  2. waitwas continued for a further hour
  3. extractionThereafter, the mixture was extracted three times with ether
  4. washthe combined ether phases were washed twice with water
  5. dry with materialdried over Na2SO4
  6. customevaporated down
  7. customRecrystallization of the residue from isopropanol

出典と根拠

ORDレコード
ord-0163cb3f970a43f794c3d4d154dccc8c
出典データセット
uspto-grants-1989_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04806558

反応ノート

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