Aluminium lithium hydride → [1-(Phenylsulfonyl)indolin-5-yl]methanol

HRID 84187Notes

Reaction equation

HRID 84187 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:15][CH2:14]2)=O>C1COCC1>[C:23]1([S:20]([N:16]2[C:17]3[C:13](=[CH:12][C:11]([CH2:9][OH:8])=[CH:19][CH:18]=3)[CH2:14][CH2:15]2)(=[O:21])=[O:22])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 31756086Methyl 1-(Phenylsulfonyl)indoline-5-carboxylate

Product 1

HCID 57517435[1-(Phenylsulfonyl)indolin-5-yl]methanolYield 65.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (0.10 g, 2.52 mmol) was added to a solution of 11 (0.40 g, 1.26 mmol) in THF (10 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 h before it was quenched with water and then extracted with CH2Cl2 (15 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The reaction mixture was purified by silica gel chromatography (EtOAc:n-hexane=1:1) to afford 12 (0.24 g). 1H NMR (500 MHz, CDCl3): δ 2.83 (t, J=8.4 Hz, 2H), 3.92 (t, J=8.5 Hz, 2H), 4.49 (s, 2H), 7.09 (s, 1H), 7.16 (d, J=8.2 Hz, 1H), 7.46-7.49 (m, 2H), 7.53 (d, J=8.2 Hz, 1H), 7.60 (t, J=7.5 Hz, 1H), 7.76 (d, J=7.7 Hz, 2H).

Workup

  1. customwas quenched with water
  2. extractionextracted with CH2Cl2 (15 mL×3)
  3. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe reaction mixture was purified by silica gel chromatography (EtOAc:n-hexane=1:1)

Sources & evidence

ORD record
ord-c821c62b4f8f4f5c9b1b716d5c8dce64
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Reaction notes

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