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Diisobutylaluminumhydride → [1-(2-Trimethylsilanyl-ethanesulfonyl)-1H-indol-5-yl]-methanol

HRID 2250157
Notes
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Reaction equation

HRID 2250157 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([S:25]([CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])(=[O:27])=[O:26])[CH:20]=[CH:19]2)=O)C>C1(C)C=CC=CC=1>[CH3:31][Si:30]([CH3:33])([CH3:32])[CH2:29][CH2:28][S:25]([N:21]1[C:22]2[C:18](=[CH:17][C:16]([CH2:14][OH:13])=[CH:24][CH:23]=2)[CH:19]=[CH:20]1)(=[O:27])=[O:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 251358641-(2-trimethylsilanylethanesulfonyl)-1H-indole-5-carboxylic acid ethyl ester

Product 1

HCID 22596206[1-(2-Trimethylsilanyl-ethanesulfonyl)-1H-indol-5-yl]-methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diisobutylaluminum hydride (82.9 mL, 1M in toluene, 82.9 mmol) was added slowly at 0° C. to the solution of 1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indole-5-carboxylic acid ethyl ester (8.81 g, 25.9 mmol) in toluene (200 mL). After it was stirred at 0° C. for 45 min, the reaction was quenched by the addition of methanol (26 mL), pulverized sodium sulfate decahydrate (194 g) and celite (26 mL). The mixture was warmed up to room temperature in 1 h and filtered through a pad of celite. Solvents were removed in vacuo to afford the title compound as a very viscous liquid, which solidified upon cooling. A white solid (8.08 g, 100% yield). 1H-NMR (CDCl3, 500 MHz) δ 7.87 (d, J=8.5 Hz, 1H), 7.62 (s, 1H), 7.44 (d, J=3.7 Hz, 1H), 7.35 (dd, J=8.6, 1.5 Hz, 1H), 6.66 (d, J=3.7 Hz, 1H), 4.79 (s, 2H), 3.18-3.14 (m, 2H), 1.73 (s, 1H), 0.85-0.82 (m, 2H), −0.06 (s, 9H). Mass spec. 312.14 (MH)+.

Workup

  1. customthe reaction was quenched by the addition of methanol (26 mL)
  2. temperatureThe mixture was warmed up to room temperature in 1 h
  3. filtrationfiltered through a pad of celite
  4. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-dd079881ccf1460882ebe523540b6b01
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07314883B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes