Dimethylformamide → (S)-(-)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-methanol

HRID 1706629Notes

Reaction equation

HRID 1706629 reaction equation
[OH:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C@:7]([CH3:16])([CH2:14][OH:15])[CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C=O)C>CCOCC.O>[CH2:24]([O:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C@:7]([CH3:16])([CH2:14][OH:15])[CH2:6][CH2:5]2)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 9881178(S)-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-methanol

Product 1

HCID 10520197(S)-(-)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.55 g. (2.33 mmol) of (S)-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-methanol, 790 mg. (5.72 mmol) of anhydrous K2CO3, 0.68 ml. (748 mg; 5.93 mmol) of benzyl chloride (distilled from and stored over K2CO3) and 4.5 ml. of DMF was stirred for 22 hrs. at room temperature then poured into H2O and worked up with ether in the usual manner. There was obtained 0.89 g. of a yellow oily product which was chromatographed on silica gel (35 g.). Elution with 19:1 and 9:1 benzene-ethyl acetate gae 724 mg. (97.1%) of (S)-(-)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-methanol as a colorless solid, mp 66°-69.5°; [α]25D-2.35° (c 1.2, CHCl3).

Workup

  1. additionA mixture of 0.55 g
  2. customThere was obtained 0.89 g
  3. customof a yellow oily product which was chromatographed on silica gel (35 g.)
  4. washElution with 19:1 and 9:1 benzene-ethyl acetate gae 724 mg

Sources & evidence

ORD record
ord-aa88f61c99c84f1b89929381ab4b6051
Source dataset
uspto-grants-1980_06
Patent number
US04208331

Reaction notes

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