Hydrochloric Acid → HCID 131715141, compound

HRID 979156Notes

Reaction equation

HRID 979156 reaction equation
[C-:1]#[N:2].C([Al+]CC)C.[CH3:8][O:9][C:10]1[CH:28]=[CH:27][C:13]2[O:14][CH2:15][C@@H:16]3[C:18]([C:23]([O:25][CH3:26])=[O:24])([C:19]([O:21][CH3:22])=[O:20])[C@@H:17]3[C:12]=2[CH:11]=1.Cl>C1(C)C=CC=CC=1>[CH3:8][O:9][C:10]1[CH:28]=[CH:27][C:13]2[O:14][CH2:15][C@@H:16]([CH:18]([C:23]([O:25][CH3:26])=[O:24])[C:19]([O:21][CH3:22])=[O:20])[C@H:17]([C:1]#[N:2])[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 16686413Diethyl aluminum cyanideHCID 131715140HCID 131715140, compound

Product 1

HCID 131715141HCID 131715141, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under nitrogen 425 ml of diethylaluminum cyanide (1.5M in toluene) is added to 93 g cis-dimethyl 1,1a,2,7b-tetrahydro-6-methoxybenzo[b]cyclopropa[d]pyran-1,1-dicarboxylate in 1250 ml toluene. After stirring 2 h at 25°, the reaction mixture is poured into 1250 ml 17.4% HCl. The aqueous phase is separated and extracted with three 100 ml portions of ethyl acetate and three 200 ml portions of CH2Cl2. The combined organic phases are washed with 500 ml 2N HCl, 500 ml brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give trans(±)-dimethyl 2-(3,4-dihydro-6-methoxy-4-cyano-2H-[1]benzopyran-3-yl)-propanedioate.

Workup

  1. customThe aqueous phase is separated
  2. extractionextracted with three 100 ml portions of ethyl acetate and three 200 ml portions of CH2Cl2
  3. washThe combined organic phases are washed with 500 ml 2N HCl, 500 ml brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dde75aceef314d3cb9dd8b0b4e33e1d2
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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