Water → (3RS,7RS,11RS)-1-(2,5-dimethoxy-3,4,6-trimethyl phenyl)-3,7,11,15-tetramethyl-3-hexadecanol

HRID 465732ノート

反応式

HRID 465732 の反応式
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH3:14].C([Li])CCC.[O:20]1[C:22]([CH3:39])([CH2:23][CH2:24][CH2:25][CH:26]([CH3:38])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:37])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:21]1.O>O1CCCC1>[CH3:12][O:11][C:6]1[C:7]([CH3:10])=[C:8]([CH3:9])[C:3]([O:2][CH3:1])=[C:4]([CH3:14])[C:5]=1[CH2:13][CH2:39][C:22]([CH3:21])([OH:20])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:38])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:37])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:35])[CH3:36]

参加物

6

反応物 4

HCID 962WaterHCID 6017651,4-Dimethoxy-2,3,5,6-tetramethylbenzeneHCID 128109942-Methyl-2-(4,8,12-trimethyltridecyl)oxiraneHCID 178418339Butyllithium

生成物 1

HCID 14631374(3RS,7RS,11RS)-1-(2,5-dimethoxy-3,4,6-trimethyl phenyl)-3,7,11,15-tetramethyl-3-hexadecanol収率 88.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1.8 g (9 mmol) of 2,5-dimethoxy-1,3,4,6-tetramethylbenzene were dissolved in 100 ml of tetrahydrofuran, treated with 1 g (9 mmol) of potassium tert.butylate and subsquently 6 ml (9.5 mmol) of n-butyllithium (1.6 molar) were added dropwise at room temperature. Thereafter, the mixture was stirred at room temperature for 30 minutes, treated dropwise with 2.7 g (9 mmol) of (2RS,6RS,10RS) -1,2-epoxy-2,6,10,14-tetramethylpentadecane and stirred at room temperature for 16 hours. Thereupon, HYFLO and 200 ml of water were added, the mixture was then filtered and washed with water. The residue was stirred up with diethyl ether and sodium sulphate, filtered, washed with diethyl ether and concentrated. There were obtained 3.8 g of (3RS,7RS,11RS)-1-(2,5-dimethoxy-3,4,6-trimethyl phenyl)-3,7,11,15-tetramethyl-3-hexadecanol.

後処理

  1. additionwere added dropwise at room temperature
  2. stirringstirred at room temperature for 16 hours
  3. filtrationthe mixture was then filtered
  4. washwashed with water
  5. stirringThe residue was stirred up with diethyl ether and sodium sulphate
  6. filtrationfiltered
  7. washwashed with diethyl ether
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-1ba9c1d3a59f4d5390f764bcb6e9a2b2
出典データセット
uspto-grants-1992_10
特許番号
US05153344

反応ノート

読み込み中…