Water → HCID 22404482, compound

HRID 259975Notes

Reaction equation

[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[CH2:10][C:11]1[C:15](=[CH2:16])[CH:14]=[CH:13][CH:12]=1.B(F)(F)F.CCOCC.O>C(Cl)Cl>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([CH2:16][C:15]2[C:11](=[CH2:10])[CH:12]=[CH:13][CH:14]=2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Anisole (0.04 mL, 0.37 mmol) was added to a solution of hydroxymethylfulvene (10 mg, 0.04 mmol) in dry CH2Cl2 (5 mL). The mixture was cooled to -78° C. and boron triflouride etherate (0.04 mL, 0.36 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, saturated NaHCO3 and brine, and dried over MgSO4. Concentration of the solution gave a residue which was dried in vacuo, yielding the product in quantitative yield (14 mg). 1H NMR δ 0.59-1.40 (m, 4 H). 1.36 (s, 3 H), 1.76 (s, 3 H), 2.07 (s, 3 H), 3.78 (s, 3 H), 3.95 (s, 1 H), 3.99 (d, J=16.12 Hz, 2 H), 6.81 (d, J=8.8 Hz, 2 H), 6.96 (d, J=8.3 Hz, 2 H), 7.22 (s, 1 H). MS m/Z 336 (M+), 308 (M+--CH2CH2), 215, 121 ((CH2 --Ph--OCH3)+). UV 410 nm (2.7×103), 325 nm (7.0×103), 267 nm (1.0×104), 245 nm (inflection), 226 nm (1.9×104), 203 nm (1.4×104). The compound has the structure: ##STR18##

Workup

customto quench
customthe reaction
washThe organic layer was washed with H2O, saturated NaHCO3 and brine
dry with materialdried over MgSO4
customConcentration of the solution gave a residue which
customwas dried in vacuo
customyielding the product in quantitative yield (14 mg)

Sources & evidence

ORD record: ord-754e9d55a52a466b874d16ed1e16f7ef
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05523490

Reaction notes

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