Water → HCID 22404481, compound

HRID 259974Notes

Reaction equation

HRID 259974 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[CH2:9][C:10]1[C:14](=[CH2:15])[CH:13]=[CH:12][CH:11]=1.B(F)(F)F.CCOCC.O>C(Cl)Cl>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([CH2:15][C:14]2[C:10](=[CH2:9])[CH:11]=[CH:12][CH:13]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 8000Boron trifluoride etherateHCID 19419368HCID 19419368, compound

Product 1

HCID 22404481HCID 22404481, compoundYield 174.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Phenol (40 mg, 0.4 mmol) was added to a solution of hydroxymethyl-fulvene (70 mg, 0.28 mmol) in dry CH2Cl2 (25 mL). The mixture was cooled to -78° C. and boron triflouride etherate (0.3 mL, 2.7 mmol) was added dropwise. The reaction was stirred at that temperature for 1 hour and water was added to quench the reaction. The organic layer was washed with H2O, NaHCO3 and brine, and dried over MgSO4. Chromatography on silica gel with hexane-ethyl acetate yielded 90 mg (98%) of red crystals (m.p. 143°-144° C.). 1H NMR δ 0.59-1.43 (m, 4 H), 1.36 (s, 3 H), 1.76 (s, 3 H), 2.07 (s, 3 H), 3.95 (s, 1 H), 3.97 (d, J=7.2 Hz, 2 H), 4.83 (s, 1 H), 6.74 (d, J=8.4 Hz, 2 H), 6.91 (d, J=8.4 Hz, 2 H), 7.22 (s, 1 H). MS m/Z 322 (M+), 294 (M+-2 CH2), 279 (M+-2 CH2 --CH3), 251 (M+-2 CH2 --CH3 --CO), 215, 107 UV 228 nm (1.2×104, with inflections at 243 and 262 nm), 325 (7.1×103), 410 nm (2.6×103). The compound has the structure: ##STR17##

Workup

  1. customto quench
  2. customthe reaction
  3. washThe organic layer was washed with H2O, NaHCO3 and brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-85604ca2d3a24e8d80fc9bd1f53c71d6
Source dataset
uspto-grants-1996_06
Patent number
US05523490

Reaction notes

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