Dimethyl Sulfide → 2-[1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl]ethanol

HRID 2301670Notes

Reaction equation

HRID 2301670 reaction equation
[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([C:24](=O)[C:25](OC)=[O:26])=[C:15]1[CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C)C>C1COCC1>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][OH:26])=[C:15]1[CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 86758767Methyl [1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl](oxo)acetate

Product 1

HCID 183732512-[1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl]ethanolYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl [1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy }methyl)-5-chloro-1H-indol-3-yl](oxo)acetate (1 eq) was dissolved in THF (0.46M), then BH3.Me2S (2M in THF) (2 eq) was added to it. The resulting mixture was refluxed with stirring overnight under N2. The reaction mixture was cooled to rt, then quenched slowly with 1N NaOH(aq). Followed by regular work-up (eg. EtOAc extraction, brine wash, etc.). Removed the solvent and purified using a column with CH2Cl2 as eluent to give 2-[1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy }methyl)-5-chloro-1H-indol-3-yl]ethanol (yellow solid) in 72% yield.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. customquenched slowly with 1N NaOH(aq)
  3. extractionFollowed by regular work-up (eg. EtOAc extraction, brine wash, etc.)
  4. customRemoved the solvent
  5. custompurified

Sources & evidence

ORD record
ord-5ecabbca6c9a42308d63bcee0a5f2140
Source dataset
uspto-grants-2002_12
Patent number
US06500853B1

Reaction notes

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