Hydrochloric Acid → HCID 12242169, compound

HRID 973871Notes

Reaction equation

HRID 973871 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:6][C:7](=[O:10])[C:8]=1[CH3:9])=[O:5].[BH4-].[Na+].Cl>C1COCC1>[OH:5][CH:4]1[O:6][C:7](=[O:10])[C:8]([CH3:9])=[C:3]1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 102908462,5-Furandione, 3-methoxy-4-methyl-

Product 1

HCID 12242169HCID 12242169, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Methoxy-3-methylmaleic anhydride (9 g), (M. M. Kayser et al, Can.J.Chem., 1986, 64, 104) in dry THF (50 mls) was added, dropwise to a suspension of sodium borohydride (1.5 g) in THF (200 mls) at 0°-5° C., over ca 30 mins. The reaction mixture was allowed to warm to room temperature for a further 30 mins. T.l.c. analysis showed no remaining starting material. The solution was carefully neutralized with 5M aqueous hydrochloric acid and then the THF removed in vacuo. The aqueous solution was extracted with ethyl acetate washed with brine and dried. After removal of solvent the crude material was purified by `flash` chromatography on silica gel eluting with 50% ethyl acetate/hexane. The title compound was obtained as a colourless crystalline solid, (6.683 g, 73%), m.p. 79° C., benzene. νmax (CH2Cl2) 3540(w), 3300 (br), 1755, 1670, 1455, 1380 and 1325cm- ; δH (CDCl 3) 1.78 (3H, s), 4.06 (3H, s), 5.96 (1H, br.s, sharpens on D2O shake) and 6.23 (1H, br.s, exch).

Workup

  1. customthe THF removed in vacuo
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washwashed with brine
  4. customdried
  5. customAfter removal of solvent the crude material
  6. customwas purified by `flash` chromatography on silica gel eluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-35def3c0f7394c13b19021ab2a1ed88d
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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