Carbon Dioxide → (Z)-3-hex-1-enyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid

HRID 619319

反応式

HRID 619319 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH3:17])[C:8]([CH3:19])([CH3:18])[CH2:7][CH2:6][C:5]2([CH3:21])[CH3:20].[Li]CCCC.[C:27](=[O:29])=[O:28]>O1CCCC1>[CH:12](/[C:11]1[C:2]([C:27]([OH:29])=[O:28])=[CH:3][C:4]2[C:5]([CH3:20])([CH3:21])[CH2:6][CH2:7][C:8]([CH3:19])([CH3:18])[C:9]=2[CH:10]=1)=[CH:13]/[CH2:14][CH2:15][CH2:16][CH3:17]

参加物

5

反応物 3

HCID 280Carbon DioxideHCID 69861084(Z)-6-bromo-7-hex-1-enyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthaleneHCID 178418339Butyllithium

生成物 1

HCID 69861266(Z)-3-hex-1-enyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3.72 g of (Z)-6-bromo-7-hex-1-enyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene (75% pure) were placed in 25 ml of abs. tetrahydrofuran and treated at -75° with 8.25 ml of 1.55M n-BuLi (hexane) (1.2 eq.). After 1/2 h., a CO2 stream was conducted vigorously through the solution for 30 min., with the temperature rising to -60° in spite of constant cooling. The mixture was left to warm to room temperature, poured on to ice/HCl solution, extracted with diethyl ether, washed with H2O, dried over Na2SO4 and the solvent was removed in a vacuum. Two-fold flash chromatography on SiO2 (hexane/ethyl acetate=85/15, then 9/1) yielded 1.06 g of (Z)-3-hex-1-enyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid as colorless crystals.

後処理

  1. customrising to -60° in spite of constant cooling
  2. waitThe mixture was left
  3. extractionextracted with diethyl ether
  4. washwashed with H2O
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed in a vacuum

出典と根拠

ORDレコード
ord-438dfe08e241443195db0c911478b102
出典データセット
uspto-grants-1999_09
特許番号
US05958956

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