HCID 13720819, compound → HCID 14882500, compound

HRID 330137Notes

Reaction equation

HRID 330137 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][CH:16]=[C:17]([C:20](OC)=[O:21])[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:17]1[CH:18]=[C:19]2[C:14]([CH:13]=[CH:12][N:11]2[S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:10])=[O:9])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 13720819HCID 13720819, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14882500HCID 14882500, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 1-(4-methylphenylsulfonyl)indole-6-carboxylate (28.0 g) in tetrahydrofuran (250 ml) was added dropwise to a slurry of lithium aluminum hydride (4.5 g) in tetrahydrofuran (300 ml) at 0°. After stirring at 0° for 15 minutes, the excess lithium aluminum hydride was quenched with a saturated solution of sodium sulfate and the resultant white precipitate was removed by filtration. The filtrate was dried (MgSO4) and evaporated to give 6-hydroxymethyl-1-(4-methylphenylsulfonyl)indole (21.5 g, 84%) as an ivory solid; partial NMR (80 MHz, CDCl3): 2.33(s, 3H, ArCH3), 4.77(d, 2H, OCH2), 6.62(dd, 1H, H3 -indole), 7.97(m, 1H, H7 -indole).

Workup

  1. customthe excess lithium aluminum hydride was quenched with a saturated solution of sodium sulfate
  2. customthe resultant white precipitate was removed by filtration
  3. dry with materialThe filtrate was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-ad6300238a774c85af721604844738e2
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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