4-Fluorophenol → 1-[(But-3-yn-1-yl)oxy]-4-fluorobenzene

HRID 2086210Notes

Reaction equation

HRID 2086210 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](O)[CH2:10][C:11]#[CH:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:11][C:10]#[CH:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 135663-Butyn-1-OLHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 222797471-[(But-3-yn-1-yl)oxy]-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Fluorophenol (5.00 g, 44.6 mmol), 3-butyn-1-ol (3.38 ml, 44.6 mmol), and triphenylphosphine (17.5 g, 66.9 mmol) were dissolved in tetrahydrofuran (100 ml), and diethyl azodicarboxylate (11.7 g, 66.9 mmol) was added thereto in an ice bath followed by stirring for 18 hours at room temperature. After the solvent was concentrated in vacuo, hexane (200 ml) and ethyl acetate (20 ml) were added thereto, and the resulting precipitate was filtered out, and then the filtrate was concentrated in vacuo. The obtained residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=1:0) to afford the title compound.

Workup

  1. customin an ice bath followed
  2. concentrationAfter the solvent was concentrated in vacuo, hexane (200 ml) and ethyl acetate (20 ml)
  3. additionwere added
  4. filtrationthe resulting precipitate was filtered out
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe obtained residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=1:0)

Sources & evidence

ORD record
ord-0562d7a898c94a6ba4b64872e7065569
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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