HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 6-Bromo-3 4-dihydro-4,4-dimethyl-8-vinylspiro[2H-1-benzopyran-2,1'-cyclopropane]
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Methylenetriphenylphosphorane | HCID 137960 | — |
| Reactant | 6-bromo-8-carbonyl-3,4-dihydro-4,4-dimethylspiro [2H-1-benzopyran-2,1'-cyclopropane] | HCID 18177968 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | 6-Bromo-3 4-dihydro-4,4-dimethyl-8-vinylspiro[2H-1-benzopyran-2,1'-cyclopropane] | HCID 22568855 | — |
Reaction Steps
Following general procedure N and using A solution of methylidene triphenyl phosphorane [generated from methyl triphenylphosphonium bromide (7 g, 20 mmol) and 1.6M solution of n-butyl lithium in hexanes (11.8 mL, 19 mmol)], 6-bromo-8-carbonyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane](Intermediate 40, 2.06 g, 7 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 1-2% ethyl acetate in hexane as the eluent, the title compound was obtained as a clear oil (1.36 g, 66%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06303785B1 |
| Source dataset | uspto-grants-2001_10 |
| ORD ID | ord-44d5811236ff4418a8d5d54849021b86 |
| Source note | uspto-grants-2001_10 |