1,2-Dimethoxyethane → 3-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)benzaldehyde

HRID 1857880ノート

反応式

HRID 1857880 の反応式
COCCOC.Br[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12].[CH3:16][C:17]1[C:18](B(O)O)=[CH:19][C:20]2[C:21]([CH3:30])([CH3:29])[CH2:22][CH2:23][C:24]([CH3:28])([CH3:27])[C:25]=2[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][C:17]1[C:18]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])=[CH:19][C:20]2[C:21]([CH3:30])([CH3:29])[CH2:22][CH2:23][C:24]([CH3:28])([CH3:27])[C:25]=2[CH:26]=1

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 765833-BromobenzaldehydeHCID 10037535(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid

生成物 1

HCID 223455053-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)benzaldehyde

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

実験手順

700 ml of DME, 2.4 g (2 mmol) of tetrakistriphenylphosphinepalladium(0) and 8.44 g (45.6 mmol) of 3-bromobenzaldehyde are introduced into a three-necked flask under a stream of nitrogen and the mixture is stirred for 10 minutes. A solution of 17 g (69.1 mmol) of 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid in 25 ml of ethanol are then added, followed by 46 ml (91 mmol) of potassium carbonate solution (2 M) and the mixture is refluxed for four hours. The reaction medium is cooled and filtered and the solid is washed with bicarbonate solution and then with ethyl acetate. The solid obtained is recrystallized from ethanol and 7 g (50%) of the expected aldehyde are collected, with a melting point of 104-5° C.

後処理

  1. temperaturethe mixture is refluxed for four hours
  2. temperatureThe reaction medium is cooled
  3. filtrationfiltered
  4. washthe solid is washed with bicarbonate solution
  5. customThe solid obtained
  6. customis recrystallized from ethanol and 7 g (50%) of the expected aldehyde
  7. customare collected, with a melting point of 104-5° C.

出典と根拠

ORDレコード
ord-95e22cd5e2164389862bf3b2c0285751
出典データセット
uspto-grants-2000_11
特許番号
US06147255

反応ノート

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