Diazomethane → HCID 13076873, compound

HRID 1438727Notes

Reaction equation

HRID 1438727 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C@H:7]([C:16]([OH:18])=[O:17])[O:8][C@H:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1.[N+](=[CH2:23])=[N-]>CCOCC>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C@H:7]([C:16]([O:18][CH3:23])=[O:17])[O:8][C@H:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 9550Diazomethane2×HCID 12812406HCID 12812406, compound

Product 1

HCID 13076873HCID 13076873, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ether solution of cis-6-chloro-4-phenyl-1,3-benzodioxan-2-carboxylic acid (2.14 g, 7.36 mmoles), chilled in an ice bath, was added an ethereal solution of diazomethane until the yellow color of the diazomethane was no longer discharged. The solution was stirred in the ice bath for 10 minutes at room temp. for 10 minutes, and finally at 35° for 15 minutes. The ether solution was washed with dil.NaHCO3 solution (2 portions), water (2 portions), and saturated brine (1 portion), and dried over anhydrous Na2SO4. The solvent was evaporated to yield a solid which was recrystallized from benzene-Skellysolve B (essentially n-hexane). The yield was 1.71 g (76%); m.p. 129.5°-131°. NMR (CDCl3), β6.6 (d, 1H, C(5)H, cis); 5.65 ppm (s, 1H, C(2)H, cis).

Workup

  1. washThe ether solution was washed with dil
  2. dry with materialNaHCO3 solution (2 portions), water (2 portions), and saturated brine (1 portion), and dried over anhydrous Na2SO4
  3. customThe solvent was evaporated
  4. customto yield a solid which
  5. customwas recrystallized from benzene-Skellysolve B (essentially n-hexane)

Sources & evidence

ORD record
ord-029b35d05f16401695956a36d38207da
Source dataset
uspto-grants-1977_11
Patent number
US04056540

Reaction notes

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