Methanol → HCID 13076878, compound

HRID 1278287Notes

Reaction equation

HRID 1278287 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][CH:7]([C:19]([OH:21])=[O:20])[O:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([CH2:10][CH:11]=[CH2:12])[C:4]=2[CH:3]=1.[Cl-].[Na+].[CH3:26]O>>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][CH:7]([C:19]([O:21][CH3:26])=[O:20])[O:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([CH2:10][CH:11]=[CH2:12])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5234Sodium ChlorideHCID 21163214HCID 21163214, compound

Product 1

HCID 13076878HCID 13076878, compound

Conditions

Temperature
20 °C

Procedure

A mixture of 20 g of the product A of Example 19, 200 ml of methanol and 6 ml of an ether-boron trifluoride complex was stirred at 20° C. for 16 hours and was then poured into a liter of aqueous saturated sodium chloride solution. The mixture was extracted with ether and the ether phase was washed with water until the wash water was neutral, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with petroleum ether (b.p.=60°-80° C.) containing 5% of ethyl acetate. The product was crystallized from methanol to obtain 3 g of isomer A of methyl 6-chloro-4-phenyl-4-(2-propenyl)-[4H]-1,3-benzodioxin-2-carboxylate melting at 70° C.

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe ether phase was washed with water until the wash water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with petroleum ether (b.p.=60°-80° C.)
  7. additioncontaining 5% of ethyl acetate
  8. customThe product was crystallized from methanol

Sources & evidence

ORD record
ord-e62dbd8a2d5742eaa814e4e9023b997e
Source dataset
uspto-grants-1981_07
Patent number
US04281012

Reaction notes

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