Methyl propionate → HCID 52046095、化合物

HRID 1907767ノート

反応式

HRID 1907767 の反応式
I[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1.[N-:12]=[N+:13]=[N-:14].[Na+].[O:16]=[C:17]1[O:23][C@H:22]([C@H](CO)O)[C:20]([O-])=[C:18]1O.[Na+].C(OC)(=O)CC>CS(C)=O.[O-]S([O-])(=O)=O.[Cu+2].O>[O:7]1[C:6]2[CH:10]=[CH:11][C:3]([CH2:2][N:12]3[CH:20]=[C:18]([C:17]([O:23][CH3:22])=[O:16])[N:14]=[N:13]3)=[CH:4][C:5]=2[O:9][CH2:8]1

参加物

8

反応物 4

HCID 11124Methyl propionateHCID 33557Sodium AzideHCID 11086556157766-09-1HCID 23667548Sodium Ascorbate

生成物 1

HCID 52046095HCID 52046095、化合物収率 611.8%

試薬・触媒・溶媒 3

HCID 24462Copper Sulfate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒2 回

実験手順

Compound 419 (1.72 g, 6.57 mmo) was dissolved in a 0.5 M solution of sodium azide 13.1 mL, 6.57 mmol) in DMSO (2 mL), stirred at room temperature overnight and quenched by pouring into a saturated solution of sodium thiosulfate. The compound was extracted with AcOEt, washed with brine, dried over MgSO4 and filtered to give a yellow solution. Water (2.5 mL) was then added followed by solid sodium ascorbate (130 mg, 0.657 mmol), methyl propionate (553 mg, 0.657 mmol) and 1M aq. CuSO4 solution (0.2 mL) to give a yellow solution. The reaction mixture was stirred overnight at room temperature to give a mustard-colored suspension. Water was added until a suspension formed, filtered, washed with water, and dried to generate the title compound 420 (1.05 g, 63% yield) as a mustard-colored solid.

後処理

  1. customquenched
  2. additionby pouring into a saturated solution of sodium thiosulfate
  3. extractionThe compound was extracted with AcOEt
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customto give a yellow solution
  8. customto give a yellow solution
  9. stirringThe reaction mixture was stirred overnight at room temperature
  10. customto give a mustard-colored suspension
  11. customformed
  12. filtrationfiltered
  13. washwashed with water
  14. customdried

出典と根拠

ORDレコード
ord-92dd77cdcd2e4fbaba8f0b004b2028e6
出典データセット
uspto-grants-2013_12
特許番号
US08598168B2

反応ノート

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