Water → [1-(4-Methylbenzene-1-sulfonyl)-1H-indol-4-yl]methanol

HRID 1903126Notes

Reaction equation

HRID 1903126 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[C:12]2[CH:13]=[CH:14][N:15]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:16]=2[CH:17]=[CH:18][CH:19]=1)=O.O>O1CCCC1>[OH:8][CH2:9][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][N:15]2[S:20]([C:23]1[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 962Water2×HCID 10947463methyl 1-tosyl-1H-indole-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12553826[1-(4-Methylbenzene-1-sulfonyl)-1H-indol-4-yl]methanolYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2nd stage: The suspension of 1.9 g of lithium-aluminum hydride in 165 ml of tetrahydrofuran cooled to 0° C. is proportionately mixed with 16.45 g of 1-tosylindole-4-carboxylic-acid-methylester. After 30 minutes 1.9 ml of water, 1.9 ml of 15% soda lye and 5.7 ml of water are carefully and sequentially dripped in. After 20 minutes, the precipitate is filtered off, washed out with acetic-acid-ethylester and the filtrates are concentrated. The raw product (15.97 g) is crystallized out of diisopropylether. 13.15 g of 4-hydroxymethyl-1-tosylindole with a m.p. of 125°-126° C. is obtained.

Workup

  1. filtrationthe precipitate is filtered off
  2. washwashed out with acetic-acid-ethylester
  3. concentrationthe filtrates are concentrated
  4. customThe raw product (15.97 g) is crystallized out of diisopropylether

Sources & evidence

ORD record
ord-042700080a9645d884a17c8b3ea7e033
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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