HCID 13720817, compound → HCID 19870636, compound

HRID 330188Notes

Reaction equation

HRID 330188 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20](OC)=[O:21])=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:21][CH2:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:11]([S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])[CH:12]=[CH:13]2

Participants

4

Reactant 2

HCID 13720817HCID 13720817, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19870636HCID 19870636, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 1-(4-methylphenylsulfonyl)indole-5-carboylate (32.2 g) in tetrahydrofuran (250 ml) was added slowly to a slurry of lithium aluminum hydride (5.2 g) in tetrahydrofuran (100 ml) at 0°. The reaction mixture was stirred 15 min at 0°, quenched with saturated sodium sulfate solution and filtered. The filtrate was dried (MgSO4) and evaporated to give 5-hydroxymethyl-1-(4-methylphenylsulfonyl)indole (21.1 g, 72%) as a white solid: NMR (80 MHz, CDCl3): 2.33(s, 3H, ArCH3), 4.74(s, 2H, OCH2), 6.64(d, 1H, H3 -indole).

Workup

  1. customquenched with saturated sodium sulfate solution
  2. filtrationfiltered
  3. dry with materialThe filtrate was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-dea4ad6c549942049393a276a113b0d9
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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