tert-Butanol → HCID 53784393, compound

HRID 1358495Notes

Reaction equation

HRID 1358495 reaction equation
[C:1]([OH:5])(C)([CH3:3])[CH3:2].[CH2:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH3:19])[CH:11]=1)CC=C.S([O-])([O-])=[O:21].[Na+].[Na+]>O>[CH3:19][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:6][CH2:2][C@H:1]([OH:5])[CH2:3][OH:21])=[CH:11]1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 181845553-(But-3-en-1-yl)-1-methyl-1H-indole

Product 1

HCID 53784393HCID 53784393, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of tert-butyl alcohol (14 ml) and water (14 ml) was added AD-mix-a (4.0 g). The mixture was stirred at room temperature until both phases are clear, and then cooled to 0° C. 3-(3-butenyl)-1-methylindole (530 mg, 2.86 mmol) was added, and the heterogeneous slurry was stirred vigorously at 0° C. for 4 hours. While the mixture was stirred at 0° C., solid sodium sulfite (4.29 g) was added and the mixture was allowed to warm to room temperature and stirred for 1 hour. This mixture was extracted with ethyl acetate, and the extracts were washed with brine, dried (magnesium sulfate) and evaporated in vacuo. The residue was purified by silica gel (15 g) chromatography eluting with chloroform/methanol (100:1 to 20:1) to give (S)-4-(1-methylindol-3-yl)butane-1,2-diol (602 mg, 96.1%).

Workup

  1. additionwas added AD-mix-a (4.0 g)
  2. temperaturecooled to 0° C
  3. stirringthe heterogeneous slurry was stirred vigorously at 0° C. for 4 hours
  4. stirringWhile the mixture was stirred at 0° C.
  5. temperatureto warm to room temperature
  6. stirringstirred for 1 hour
  7. extractionThis mixture was extracted with ethyl acetate
  8. washthe extracts were washed with brine
  9. dry with materialdried (magnesium sulfate)
  10. customevaporated in vacuo
  11. customThe residue was purified by silica gel (15 g) chromatography
  12. washeluting with chloroform/methanol (100:1 to 20:1)

Sources & evidence

ORD record
ord-719eaf0b719e4e90bbce98fa4137b089
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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