Dimethyl Sulfate → HCID 20029816, compound

HRID 568874Notes

Reaction equation

HRID 568874 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. ca20°. 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-c89bf0a41a96496db91e82bcbe2073d8
Source dataset
uspto-grants-1988_03
Patent number
US04730008

Reaction notes

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