HuagongsheHuagongshe Chemistry Print Report · For research reference only
Allyl bromide → racemic-3,4-dihydro-2,5,7,8-tetramethyl-6-(2-propenyloxy)-2H-1-benzopyran-2-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Allyl bromide | HCID 7841 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-acetate | HCID 13909413 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | racemic-3,4-dihydro-2,5,7,8-tetramethyl-6-(2-propenyloxy)-2H-1-benzopyran-2-acetic acid methyl ester | HCID 54012058 | 83.1% |
Reaction Steps
Using the procedure of Example 12, 1.42 g of racemic-3,4-dihydro-2,5,7,8-tetramethyl-6-hydroxy-2H-1-benzopyran-2-acetic acid methyl ester was alkylated with allyl bromide (2.79 g) and sodium hydride (5.58 mmole) in anhydrous N,N-dimethylformamide. There was obtained 1.35 g (83.1%) of racemic-3,4-dihydro-2,5,7,8-tetramethyl-6-(2-propenyloxy)-2H-1-benzopyran-2-acetic acid methyl ester as a yellow oil, after column chromatographic purification (silica gel, 9:1 hexane-ethyl acetate).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04785017 |
| Source dataset | uspto-grants-1988_11 |
| ORD ID | ord-e9ac66453ea04299a646f3774a832c3d |
| Source note | uspto-grants-1988_11 |