Diethyl Ether → 4-[2-[(E)-2-iodovinyl]-phenoxy]-butan-1-ol

HRID 2081320Notes

Reaction equation

HRID 2081320 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:15]=[CH:16]/[I:17])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C>O1CCCC1>[I:17]/[CH:16]=[CH:15]/[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][CH2:4][OH:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 150701204-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 150701424-[2-[(E)-2-iodovinyl]-phenoxy]-butan-1-olYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 250 mg of 4-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid ethyl ester in 5 ml of tetrahydrofuran is instilled into a suspension of 80 mg of lithium aluminum hydride at 0° C. with stirring and under argon atmosphere. Then, it is stirred for an hour with ice cooling, the mixture is decomposed under argon atmosphere with ice water, shaken out with diethyl ether, dried (Na2SO4) and concentrated by evaporation. 120 mg of 4-[2-[(E)-2-iodovinyl]-phenoxy]-butan-1-ol is obtained as a yellow oil, which is further reacted as a crude product.

Workup

  1. stirringThen, it is stirred for an hour with ice cooling
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-042a509286504dbda294c99e3f1377be
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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