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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 1380683
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HRID 1380683 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 104815
Copper(1+)
촉매
HCID 3283Diethyl Ether용매

실험 절차

5.8 mmol of (3R,7R)-3,7,11-trimethyl-dodecyl bromide were heated at reflux in 20 ml of ethyl ether for 0.25 hour with calcinated magnesium. 1 g of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxybutane and 0.9 g of copper (I) 2-propylacetylide [or 1.2 g of copper (I) bromide-dimethyl sulphide complex] were than added at 0° C. The temperature of the mixture was subsequently left to rise to room temperature and the mixture was stirred overnight. 10 ml of ammonium chloride were then added and the mixture was extracted with ethyl ether. The extract was dried, concentrated and distilled in a bulb-tube (b.p.0.01 =140° C.). There were 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-tetramethylhexadecan-3-ol as a colourless oil. [α]D20 -0.67° (c=0.9% in chloroform).

후처리

  1. additionthan added at 0° C
  2. waitThe temperature of the mixture was subsequently left
  3. customto rise to room temperature
  4. extractionthe mixture was extracted with ethyl ether
  5. customThe extract was dried
  6. concentrationconcentrated
  7. distillationdistilled in a bulb-tube (b.p.0.01 =140° C.)

출처 및 근거

ORD 기록
ord-d36b2b5c21ec47d48bc5ba62b8081aa4
출처 데이터셋
uspto-grants-1986_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04582919

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