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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
Notes
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Reaction equation

HRID 1789604 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents

2
HCID 104815Copper(1+)CatalystHCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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.)

Sources & evidence

ORD record
ord-5b0c068bddba4660a3c804cef037e9b1
Source dataset
uspto-grants-1987_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04689427

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes