Acetic Acid → 7-(Hydroxymethyl)-2,3-dihydro-5(1H)-indolizinone

HRID 15352Notes

Reaction equation

HRID 15352 reaction equation
CC([Si](C)(C)[O:6][CH2:7][C:8]1[CH:16]=[C:15]2[N:11]([CH2:12][CH2:13][CH2:14]2)[C:10](=[O:17])[CH:9]=1)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:6][CH2:7][C:8]1[CH:16]=[C:15]2[N:11]([CH2:12][CH2:13][CH2:14]2)[C:10](=[O:17])[CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 574868927-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-2,3-dihydro-5(1H)-indolizinone

Product 1

HCID 574868937-(Hydroxymethyl)-2,3-dihydro-5(1H)-indolizinoneYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2,3-dihydro-5(1H)-indolizinone (3.93 g, 14.09 mmol) in tetrahydrofuran (100 ml) was treated with acetic acid (1.61 ml, 28.17 mmol) and tetrabutylammonium fluoride (1M in THF, 21 ml, 21.13 mmol) and stirred at room temperature for 1 h before being evaporated. The residue was chromatographed on silica eluting with 0-20% methanol in dichloromethane to give the desired product (1.87 g, 80%)

Workup

  1. custombefore being evaporated
  2. customThe residue was chromatographed on silica eluting with 0-20% methanol in dichloromethane

Sources & evidence

ORD record
ord-220eb772aa9a42cdbc85e33000ec2cfa
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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