Phenol → HCID 178516307, compound

HRID 70742Notes

Reaction equation

HRID 70742 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]=2)=[CH:2]1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.B(F)(F)F.C(Cl)Cl>CCOC(C)=O>[OH:18][C:12]1[CH:17]=[CH:16][C:15]([SH:1]2[CH:5]=[CH:4][C:3]([CH:6]3[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]3)=[CH:2]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 6344DichloromethaneHCID 6356Boron trifluorideHCID 126474723-(Cyclohex-1-en-1-yl)thiophene

Product 1

HCID 178516307HCID 178516307, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Thiophene-3-yl cyclohexene (72.3 mg, 0.44 mmol), and phenol (82.8 mg, 0.88 mmol) was mixed and gently heated until uniform and BF3*H3PO4 (4 uL, 0.044 mmol) was added. The mixture was heated at 70° C. overnight and the dark residue was diluted with EtOAc, washed with sat. NaHCO3, dried and concentrated. Column chromatography (silica, 0-20% EtOAc) gave a mixture of isomers and the desired product could be isolated by preparative TLC (DCM eluent). Yield: 3.7 mg, off-white/pale yellow solid. GC-MS: M+=258.

Workup

  1. additionwas added
  2. washwashed with sat. NaHCO3
  3. customdried
  4. concentrationconcentrated
  5. customColumn chromatography (silica, 0-20% EtOAc) gave
  6. additiona mixture of isomers

Sources & evidence

ORD record
ord-a47abaa40f0f4c32b39487541dddc4d0
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Reaction notes

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