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

HRID 1085208ノート

反応式

HRID 1085208 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-85bc89c436ea4c20910a8c5ca5e96a62
出典データセット
uspto-grants-1991_04
特許番号
US05008281

反応ノート

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