Tetrabutylammonium Fluoride → HCID 18373336, compound

HRID 2301673Notes

Reaction equation

HRID 2301673 reaction equation
[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][S:26]([C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[C:15]1[CH2:39][O:40][Si](C(C)(C)C)(C)C)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][S:26]([C:29]2[CH:30]=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][CH:38]=2)(=[O:28])=[O:27])=[C:15]1[CH2:39][OH:40])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70159265HCID 70159265, compound

Product 1

HCID 18373336HCID 18373336, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-({2-[1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl]ethyl}sulfonyl)benzoate (1 eq) was dissolved in THF (0.3M), followed by nBu4NF (1M in THF) (1.2 eq). The resulting mixture was stirred at rt for 3 hrs, then quenched with NH4Cl(aq). Extracted with EtOAc and washed with brine. Purified with prep plate and 1:3 EtOAc/Hexane as eluent to give methyl 4-({2-[1-benzhydryl-5-chloro-2-(hydroxymethyl)-1H-indol-3-yl]ethyl}sulfonyl)benzoate (light brown gum) in 95% yield.

Workup

  1. customquenched with NH4Cl(aq)
  2. extractionExtracted with EtOAc
  3. washwashed with brine
  4. customPurified with prep plate and 1:3 EtOAc/Hexane as eluent

Sources & evidence

ORD record
ord-d6cf4ed991ce46b8923b3392bfa0763f
Source dataset
uspto-grants-2002_12
Patent number
US06500853B1

Reaction notes

Loading…