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Ammonium Chloride → (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethylhexadecan-3-ol

HRID 1789604
ノート
印刷プレビュー

反応式

HRID 1789604 の反応式
[CH3:1][C@H:2]([CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:3][CH2:4]Br.[Mg].[CH3:18][O:19][C:20]1[C:25]([CH3:26])=[C:24]([CH3:27])[C:23]([O:28][CH3:29])=[C:22]([CH3:30])[C:21]=1[CH2:31][CH2:32][C@:33]1([CH3:36])[O:35][CH2:34]1.[Cl-].[NH4+]>C(OCC)C.[Cu+]>[CH3:18][O:19][C:20]1[C:25]([CH3:26])=[C:24]([CH3:27])[C:23]([O:28][CH3:29])=[C:22]([CH3:30])[C:21]=1[CH2:31][CH2:32][C@:33]([CH3:36])([OH:35])[CH2:34][CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 13191851(3R,7R)-1-bromo-3,7,11-trimethyldodecaneHCID 18602184(S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxy-butane

生成物 1

HCID 14631375(3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethylhexadecan-3-ol

試薬・触媒・溶媒 2

HCID 104815
Copper(1+)
触媒
HCID 3283Diethyl Ether溶媒

実験手順

5.8 mmol of (3R,7R)-3,7,11-trimethyl-dodecyl bromide are heated at reflux for 1/4 hour in 20 ml of diethyl ether with etched magnesium. 1 g of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxy-butane and 0.9 g of copper(I) 2-propylacetylide (or 1.2 g of copper(I) bromide-dimethyl sulphide complex) are then added at 0° C. The temperature of the reaction mixture is subsequently left to rise to room temperature and the mixture is stirred for about 16 hours. 10 ml of ammonium chloride are then added and the mixture is extracted with diethyl ether. The extract is dried, concentrated and distilled in a bulb-tube (b.p.0.01 =140° C.). There are obtained 1.28 g (72%) [or 1.41 g (79%)] of (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol as a colourless oil, [α]D20 -0.67° (c=0.9% in CHCl3).

後処理

  1. waitThe temperature of the reaction mixture is subsequently left
  2. customto rise to room temperature
  3. extractionthe mixture is extracted with diethyl ether
  4. customThe extract is dried
  5. concentrationconcentrated
  6. distillationdistilled in a bulb-tube (b.p.0.01 =140° C.)

出典と根拠

ORDレコード
ord-5b0c068bddba4660a3c804cef037e9b1
出典データセット
uspto-grants-1987_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04689427

反応ノート

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