Hydrochloric Acid → 4-Hydroxymethyl-2-((Z)-2-tritylthioethen-1-yl)thiazole

HRID 1799680ノート

反応式

HRID 1799680 の反応式
C[O:2][C:3]([C:5]1[N:6]=[C:7](/[CH:10]=[CH:11]\[S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.O.Cl>ClCCl>[OH:2][CH2:3][C:5]1[N:6]=[C:7](/[CH:10]=[CH:11]\[S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:8][CH:9]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 686011224-methoxycarbonyl-2-((Z)-2-tritylthioethen-1-yl)thiazoleHCID 86583787Diisobutylaluminumhydride toluene

生成物 1

HCID 686009804-Hydroxymethyl-2-((Z)-2-tritylthioethen-1-yl)thiazole収率 88.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 3.48 g of 4-methoxycarbonyl-2-((Z)-2-tritylthioethen-1-yl)thiazole in 70 ml of dichloromethane was cooled in ice, and 18.7 ml of a 1.0 M diisobutylaluminum hydride/toluene solution was added dropwise to the cooled solution under an argon atmosphere. The mixture was stirred at the same temperature for one hr. Water was then added to the reaction solution, and the mixture was adjusted to pH 2.5 by the addition of 1 N aqueous hydrochloric acid. The insolubles were removed by filtration through Celite, and the filtrate was extracted twice with ethyl acetate. The organic layers were combined, were washed with brine, were dried over anhydrous magnesium sulfate, were filtered, and were concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 2.88 g of the title compound.

後処理

  1. customThe insolubles were removed by filtration through Celite
  2. extractionthe filtrate was extracted twice with ethyl acetate
  3. washwere washed with brine
  4. dry with materialwere dried over anhydrous magnesium sulfate
  5. filtrationwere filtered
  6. concentrationwere concentrated under the reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-8d6f03afa3cd43a1b6b1b5045a8b2521
出典データセット
uspto-grants-2013_01
特許番号
US08344154B2

反応ノート

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