tert-Butanol → (S)-1-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethane-1,2-diol

HRID 1468679Notes

Reaction equation

HRID 1468679 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[S:15][CH:14]=[N:13][C:12]=3[CH:11]=[C:10](C)[C:9]=2C=C)=[CH:4][CH:3]=1.S([O-])([O-])=[O:21].[Na+].[Na+].[C:26]([OH:30])(C)([CH3:28])[CH3:27]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[S:15][CH:14]=[N:13][C:12]=3[CH:11]=[C:10]([CH3:9])[C:27]=2[C@H:26]([OH:30])[CH2:28][OH:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 891577997-(4-Chlorophenyl)-5-methyl-6-vinylbenzo[d]thiazole

Product 1

HCID 70981470(S)-1-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethane-1,2-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A biphasic mixture of AD mix-α (1.5 g) in tert-butanol (5 mL)/H2O (5 mL) was cooled to 0° C. and 7-(4-chlorophenyl)-5-methyl-6-vinylbenzo[d]thiazole (5G) (0.050 g, 0.175 mmol) was added. Reaction mixture was stirred overnight at 0° C. Sodium sulfite (1.5 g) was added at 0° C., then warmed to room temperature and stirred for 30 min to give a white mixture. Mixture was diluted with ethyl ecetate and H2O. Extracted with ethyl ecetate (3×) and combined organic layer was dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give the product.

Workup

  1. customReaction mixture
  2. temperaturewarmed to room temperature
  3. stirringstirred for 30 min
  4. customto give a white mixture
  5. extractionExtracted with ethyl ecetate (3×)
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)
  9. customto give the product

Sources & evidence

ORD record
ord-e3d76cdcf3964026b1846629c1a8a587
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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