Chlorotrimethylsilane → (S)-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1,2-butanediol

HRID 1789601Notes

Reaction equation

HRID 1789601 reaction equation
[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[CH2:14][C@H:15]1[O:20][C@:16]1([CH3:19])[CH2:17][OH:18].C[Si](C)(C)Cl.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[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[CH2:14][CH2:15][C@:16]([CH3:19])([OH:20])[CH2:17][OH:18]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 18602181(2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methylbutanol

Product 1

HCID 11129761(S)-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1,2-butanediol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.10 g of (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methylbutanol are dissolved in 2 ml of pyridine. 0.5 ml of trimethylchlorosilane is then added and the mixture is left to stand at room temperature for 1 hour. Thereupon, sodium bicarbonate solution is added and the mixture is extracted with toluene. The combined organic phases are dried over anhydrous sodium sulphate and concentrated. The thus-obtained (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methyl-1-(trimethylsilyloxy)-butane is dissolved in 10 ml of diethyl ether, treated with 40 mg of lithium aluminum hydride and stirred at room temperature for 16 hours. Ammonium hydrogen difluoride solution is then added and the mixture is subsequently extracted with ethyl acetate. The combined organic phases are dried over anhydrous sodium sulphate and concentrated, and the residue is dried further in a higher vacuum. There are thus obtained 804 mg (73%) of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-butanediol, m.p. 86°-87° C., [α]D20 +2.53° (c=5.3% in CHCl3).

Workup

  1. waitthe mixture is left
  2. extractionthe mixture is extracted with toluene
  3. dry with materialThe combined organic phases are dried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. dissolutionThe thus-obtained (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methyl-1-(trimethylsilyloxy)-butane is dissolved in 10 ml of diethyl ether
  6. additiontreated with 40 mg of lithium aluminum hydride
  7. additionAmmonium hydrogen difluoride solution is then added
  8. extractionthe mixture is subsequently extracted with ethyl acetate
  9. dry with materialThe combined organic phases are dried over anhydrous sodium sulphate
  10. concentrationconcentrated
  11. customthe residue is dried further in a higher vacuum

Sources & evidence

ORD record
ord-f8f528d14d0e4430996d206144ceb5bb
Source dataset
uspto-grants-1987_08
Patent number
US04689427

Reaction notes

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