Hexane → Ethyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)propiolate

HRID 428230

反応式

HRID 428230 の反応式
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=2[CH:4]=1)#[CH:2].C([Li])CCC.CCCCCC.[CH2:28]([O:30][C:31](Cl)=[O:32])[CH3:29]>CCOCC>[CH3:13][C:9]1([CH3:14])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]2[CH:4]=[C:3]([C:1]#[C:2][C:31]([O:30][CH2:28][CH3:29])=[O:32])[CH:12]=[CH:11][C:10]1=2

参加物

6

反応物 4

HCID 8058HexaneHCID 10928Ethyl chloroformateHCID 147265491,1,4,4-Tetramethyl-6-ethynyl-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

生成物 1

HCID 11000580Ethyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)propiolate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-10 °C

実験手順

To a cold solution (−78° C.) of 2-ethynyl,5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (900 mgs, 4.3 mmols) in ether (20 ml) was added n-butyllithium in hexane (5.6 mmols). The mixture was stirred for 45 mins, and ethylchloroformate (1.3 g, 12 mmols) was added via syringe. Stirring was continued for 45 mins then the mixture was warmed gradually to −10° C. and quenched by adding sodium bicarbonate (NaHCO3) solution (10 ml). Diethyl ether (100 ml) was added, the organic phase washed with water (10 ml), brine (10 ml), and dried (MgSO4). The solvent was removed in vacuo. Purification of the residue over silicagel (5% ethylacetate in hexane) gave the title compound as a colorless oil.

後処理

  1. stirringStirring
  2. waitwas continued for 45 mins
  3. customquenched
  4. additionby adding sodium bicarbonate (NaHCO3) solution (10 ml)
  5. additionDiethyl ether (100 ml) was added
  6. washthe organic phase washed with water (10 ml), brine (10 ml)
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customPurification of the residue over silicagel (5% ethylacetate in hexane)

出典と根拠

ORDレコード
ord-3e8e7146651c4e688d91778793842f9c
出典データセット
uspto-grants-2001_11
特許番号
US06313163B1

関連ノート

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