2-(Trimethylsilyl)ethanol → Trimethylsilanylethyl 2-fluoro-4-iodobenzoate

HRID 635558Notes

Reaction equation

HRID 635558 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][Si:13]([CH3:18])([CH3:17])[CH2:14][CH2:15]O>ClCCl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:15][CH2:14][Si:13]([CH3:18])([CH3:17])[CH3:12])=[O:5]

Participants

5

Reactant 2

HCID 180132-(Trimethylsilyl)ethanolHCID 27745162-Fluoro-4-iodobenzoic acid2×

Product 1

HCID 54147505Trimethylsilanylethyl 2-fluoro-4-iodobenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 115.5 mg (0.4 mmol) of 2-fluoro-4-iodobenzoic acid (Compound B) in 10 mL of dichloromethane (under a blanket of argon) was added 91.5 mg (0.5 mmol) of 1-(3-dimethylaminopropyl-3-ethyl carbodiimide hydrochloride) and 53 mg (0.4 mmol) of 4-dimethylaminopyridine. To this reaction mixture was added 0.16 ml (132 mg, 1.1 mmol) of 2-trimethylsilylethanol and the resultant mixture was allowed to stir at ambient temperature for 23 hours. The reaction mixture was extracted between ethyl ether and water and the layers were separated. The aqueous phase was washed with ethyl ether (2×50 mL) and the organic phases were combined. The combined organic phase was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to a clear, colorless oil. Purification by flash chromatography (silica, 3% ethyl acetate in hexane) gave the title compound as a clear, colorless oil. PMR (CDCl3): δ 0.07 (9 H, s), 1.13 (2 H, dd, J=8.5, 10.3 Hz), 4.42 (2 H, q, J=8.5, 10.3 Hz), 7.50-7.70 (3 H, m).

Workup

  1. extractionThe reaction mixture was extracted between ethyl ether and water
  2. customthe layers were separated
  3. washThe aqueous phase was washed with ethyl ether (2×50 mL)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a clear, colorless oil
  8. customPurification by flash chromatography (silica, 3% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a7b29c0ceadd4fdea1f140e83e0ed28e
Source dataset
uspto-grants-2001_02
Patent number
US06187950B1

Reaction notes

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