HCID 11089256, compound → HCID 22025357, compound

HRID 1792846Notes

Reaction equation

HRID 1792846 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]([C:15]1[C:16]2[CH:17]=[CH:18][N:19]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:20]=2[C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)=O>C(Cl)Cl.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>[C:29]1([S:26]([N:19]2[C:20]3[C:16](=[C:15]([CH2:13][OH:12])[CH:23]=[CH:22][C:21]=3[O:24][CH3:25])[CH:17]=[CH:18]2)(=[O:28])=[O:27])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 11089256HCID 11089256, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 22025357HCID 22025357, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 9357Potassium Sodium TartrateSolvent

Procedure

Diisobutylaluminum hydride (1.5 M toluene, 1.4 mL, 2.1 mmol) is added dropwise to a −78° C. solution of 1-benzenesulfonyl-7-methoxy-1H-indole-4-carboxylic acid methyl ester (0.34 g, 0.98 mmol, Santangelo, et. al., Synth. Commun. 1993, 23, 2717–2725) in CH2Cl2 (7 mL). After stirring for 1 h, the solution is diluted with 10% aq. Rochelle's salt (100 mL) and extracted twice with EtOAc (100 mL). The organics are washed with aq. Rochelle's salt and brine. The organics are dried (MgSO4) and concentrated under reduced pressure to provide (1-benzenesulfonyl-7-methoxy-1H-indol-4-yl)-methanol as a crispy foam which is used as is without further purification.

Workup

  1. extractionextracted twice with EtOAc (100 mL)
  2. washThe organics are washed with aq. Rochelle's salt and brine
  3. dry with materialThe organics are dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dcdc731f2cc84ee29c862d4a72fe44ae
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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