Dimethyl Sulfate → HCID 20029816, compound

HRID 1721901Notes

Reaction equation

HRID 1721901 reaction equation
COS([O:6][CH3:7])(=O)=O.[I:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17]O)=[CH:11][CH:10]=1.[OH-].[Na+].[OH-].[NH4+]>>[I:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][O:6][CH3:7])=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 15789203HCID 15789203, compound

Product 1

HCID 20029816HCID 20029816, compoundYield 92%

Procedure

Dimethylsulphate (2.2 g) was added dropwise over 5 min to a vigorously stirred mixture of the product of stage (i) (3.0 g), TAB (0.15 g) 50% w/v aqueous sodium hydroxide (2.8 ml) in H (10 ml) and MC (5 ml) and stirring was continued for a further 2.5 h. Concentrated ammonium hydroxide solution (5 ml) was added and the mixture was stirred for 30 min to destroy the excess dimethylsulphate. Water (50 ml) was added, the mixture extracted with ER (2×35 ml), the organic layer dried and concentrated in vacuo at 35° to afford a brown oil. This was purified by FCC eluting with ER-CX (1:10) yielding the title compound as a cream crystalline solid (2.91 g) m.p. ca 20°. T.l.c. (ER-H 1:8) Rf 0.44.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customto destroy the excess dimethylsulphate
  3. additionWater (50 ml) was added
  4. extractionthe mixture extracted with ER (2×35 ml)
  5. customthe organic layer dried
  6. concentrationconcentrated in vacuo at 35°
  7. customto afford a brown oil
  8. customThis was purified by FCC
  9. washeluting with ER-CX (1:10)

Sources & evidence

ORD record
ord-28153b9ebc37485b8d18188eb5569309
Source dataset
uspto-grants-1989_08
Patent number
US04853382

Reaction notes

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