Boron trifluoride etherate → 3-(2-propynyl)-5-hydroxymethyl-2-(3H)-thiazolone

HRID 1650743노트

반응식

HRID 1650743 반응식
[O:1]=[C:2]1[N:6]([CH2:7][C:8]#[CH:9])[CH:5]=[C:4]([C:10](OCC)=[O:11])[S:3]1.B(F)(F)F.CCOCC.[H-].C([Al+]CC(C)C)C(C)C.[K].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:7]([N:6]1[CH:5]=[C:4]([CH2:10][OH:11])[S:3][C:2]1=[O:1])[C:8]#[CH:9]

참가 물질

7

반응물 5

HCID 8000Boron trifluoride etherateHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 5462222PotassiumHCID 14457166HCID 14457166, 화합물HCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 144571623-(2-propynyl)-5-hydroxymethyl-2-(3H)-thiazolone수율 34.5%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

A solution of 8.44 g of the product of Step B in 100 ml of toluene was cooled to -65° C. to -70° C. and 5.6 g of boron trifluoride etherate were added. The mixture was stirred for 30 minutes and 200 ml of a 1.2M solution of diisobutyl aluminium hydride in toluene were introduced over 2 hours 15 minutes. Stirring was carried out for a further 30 minutes and the mixture was poured into 1.5 l of a M solution of potassium and sodium tartrate. After stirring for one hour and decanting, extraction was carried out with ethyl acetate. The extracts were washed with water saturated with sodium chloride, dried and brought to dryness. The residue was chromatographed and elution with a hexane-chloroform-acetone mixture (6-2-2) yielded. 2.33 g of the expected product melting at 97° to 98° C.

후처리

  1. stirringStirring
  2. waitwas carried out for a further 30 minutes
  3. stirringAfter stirring for one hour
  4. customdecanting
  5. extractionextraction
  6. washThe extracts were washed with water saturated with sodium chloride
  7. customdried
  8. customThe residue was chromatographed
  9. washelution with a hexane-chloroform-acetone mixture (6-2-2)
  10. customyielded

출처 및 근거

ORD 기록
ord-28902628b5804573891c929cf6b642b6
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04925862

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