2,3-Dihydroxybutanedioic Acid → 4-Formylbenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

HRID 2256852ノート

反応式

HRID 2256852 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]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]#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].S([O-])([O-])(=O)=O.[Na+].[Na+]>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]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH:32]=[O:37])=[CH:28][CH:27]=3)[CH:15]=[CH:14][C:13]1=2

参加物

6

反応物 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 24436Sodium SulfateHCID 148505774-Cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl etherHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 148505794-Formylbenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
25 °C

実験手順

15.5 ml (19.7 mmol) of diisobutylaluminum hydride solution (20% in hexane) were added dropwise under nitrogen to a solution of 3 g (9.4 mmol) of 4-cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether in 40 ml of dry ether at 25° C. The mixture was stirred at 25° C. for 40 min and then 250 ml of saturated tartaric acid solution were added dropwise. Subsequently, a little sodium sulfate solution was added, and the phases were separated. The aqueous phase was extracted with ether, and the organic extract was washed with saturated tartaric acid solution and water, dried over Na2SO4 and concentrated. Recrystallization from methanol resulted in 1.4 g of the title compound of melting point 102°-104° C.

後処理

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with ether
  3. extractionthe organic extract
  4. washwas washed with saturated tartaric acid solution and water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customRecrystallization from methanol

出典と根拠

ORDレコード
ord-63029336d8644a1c92e06ef4cac1519f
出典データセット
uspto-grants-1997_08
特許番号
US05656619

反応ノート

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