Iodoethane → HCID 21938712, compound

HRID 1242261Notes

Reaction equation

HRID 1242261 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:15][CH3:16]>CN(C=O)C.O>[CH2:15]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1)[CH3:16]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 824523-(4-Hydroxyphenyl)propanol

Product 1

HCID 21938712HCID 21938712, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-hydroxyphenyl)-1-propanol (3.00 g, 19.7 mmol, 1 equiv) in DMF (100 ml) was added portion wise NaH (0.45 g, 18.8 mmol, 0.95 equiv) at rt, and the resulting mixture was stirred for 15 min. Iodoethane (1.37 ml, 20.0 mmol, 1 equiv) was added drop wise and the mixture was stirred for 2.5 h. The reaction mixture was diluted with water and extracted with EtOAc. The extract was washed with water, dried over MgSO4, and concentrated under vacuum to give the title compound (2.90 g, 81.7%) that was used as such for the next step.

Workup

  1. stirringthe mixture was stirred for 2.5 h
  2. extractionextracted with EtOAc
  3. washThe extract was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d5620051d5814d10bfa2bc70dd79f134
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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