Hydrochloric Acid → HCID 18972290, compound

HRID 2394217Notes

Reaction equation

HRID 2394217 reaction equation
[C:1]1([C:7]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:12][C:11]3[C:13]4[C:18]([C:19](OC)=[C:20]([C:21]([O:23][CH3:24])=[O:22])[C:10]=3[CH:9]=[CH:8]2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CC[CH2:35][CH2:34]1.C([Mg]Br)=C.Cl>CCOCC>[C:1]1([C:7]2([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[O:12][C:11]3[C:13]4[C:18]([C:19]([CH:34]=[CH2:35])=[C:20]([C:21]([O:23][CH3:24])=[O:22])[C:10]=3[CH:9]=[CH:8]2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 19359120HCID 19359120, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 18972290HCID 18972290, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,2-diphenyl-5-methoxycarbonyl-6-methoxy-2H-naphtho[1,2-b]pyran (4.22 grams) was added to a reaction flask containing tetrahydrofuran (THF) (50 milliliters (mL)). Vinyl magnesium bromide solution (20 mL of 2.0 molar in tetrahydrofuran) was injected slowly into the solution. After stirring at room temperature for two hours, the reaction mixture was poured into a beaker containing a mixture of ice, hydrochloric acid and ether. The ether layer was separated, washed with water twice and dried over anhydrous sodium sulfate. The reaction product was induced to crystallize from an ether/hexane mixture yielding 2.95 grams of 2,2-diphenyl-5-methoxycarbonyl-6-vinyl-2H-naphtho[1,2-b]pyran which was used directly in the next step.

Workup

  1. additionthe reaction mixture was poured into a beaker
  2. additioncontaining
  3. customThe ether layer was separated
  4. washwashed with water twice
  5. dry with materialdried over anhydrous sodium sulfate
  6. customto crystallize from an ether/hexane mixture

Sources & evidence

ORD record
ord-dad4b90b87df4dfe8d60ccf16ec86482
Source dataset
uspto-grants-1998_09
Patent number
US05811034

Reaction notes

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