Oxalyl chloride → 2,2,2-Triphenylacetyl chloride

HRID 232372ノート

反応式

HRID 232372 の反応式
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:26])=O>C1C=CC=CC=1.CN(C)C=O>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([Cl:26])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 2

HCID 65578Oxalyl chlorideHCID 68992Triphenylacetic acid

生成物 1

HCID 3472012,2,2-Triphenylacetyl chloride

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 241Benzene溶媒

実験手順

A slurry of 0.4 g of triphenylacetic acid in 10 ml of benzene was stirred at 25° C. and treated with 0.2 g of oxalyl chloride and 1 drop of dimethylformamide. Effervesence occurred over a period of about 30 minutes, after which time a solution was obtained. This solution was left to stand at room temperature for 1.5 hours and was then evaporated to give triphenylacetyl chloride in the form of an oil. The acid chloride was cooled to about -10° C. by means of an ice/salt bath and 10 ml of dry pyridine and 0.36 g of 5'-amino-2',5'-dideoxy-5-ethyluridine were added. The mixture was shaken for about 15 minutes, whereby the acid chloride dissolved and the temperature rose to 0° C. The solution was then stirred at 0° C. for 4 hours and then evaporated. The residue was re-evaporated three times with toluene, there being obtained a gum which was triturated with 20 ml of water to give 0.66 g of a solid of melting point 110°-140° C. Recrystallization from 12 ml of ethanol removed residual triphenylacetic acid and the residue was chromatographed on a column of silica gel using methylene chloride/methanol (9:1) for the elution. Recrystallization from a mixture of 5 ml of toluene, 10 ml of cyclohexane and 0.1 ml of ethyl acetate gave 0.25 g of 2',5'-dideoxy-5-ethyl-5'-(triphenylacetamido)uridine of melting point about 110°-120° C. (decomposition).

後処理

  1. customafter which time a solution was obtained
  2. waitThis solution was left
  3. waitto stand at room temperature for 1.5 hours
  4. customwas then evaporated

出典と根拠

ORDレコード
ord-1e601f340c3d4a659113292f4398fa57
出典データセット
uspto-grants-1989_07
特許番号
US04851519

反応ノート

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