Thiazole → Ethyl 4-[hydroxy(1,3-thiazol-2-yl)methyl]cyclohexanecarboxylate

HRID 928101ノート

反応式

HRID 928101 の反応式
C([Mg]Cl)(C)C.[Li+].[Cl-].[S:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.[CH:13]([CH:15]1[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:14]>C1COCC1>[OH:14][CH:13]([C:9]1[S:8][CH:12]=[CH:11][N:10]=1)[CH:15]1[CH2:16][CH2:17][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:20]1

参加物

5

反応物 3

HCID 9256ThiazoleHCID 13548164(1R,4R)-Ethyl 4-formylcyclohexanecarboxylateHCID 178461733HCID 178461733、化合物

生成物 1

HCID 70983583Ethyl 4-[hydroxy(1,3-thiazol-2-yl)methyl]cyclohexanecarboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

To a 500 mL round bottom flask was added iPrMgCl-LiCl (1.3 M in THF, 99 mL, 129 mmol) and the solution cooled in an ice bath. Thiazole (9.7 mL, 135 mmol) was then introduced at such a rate that the internal temperature did not exceed 5° C. and then the thick slurry was stirred for 1 h. 100 mL of THF was introduced and the reaction mixture cooled to −50° C. at which point ethyl 4-formylcyclohexanecarboxylate (23 g) was added as a solution in THF (100 mL) via cannula. When complete the reaction mixture was permitted to warm slowly to 5° C. where it was stirred for 30 min then quenched by the addition of water and EtOAc. The layers were separated, the organic mixture dried with MgSO4, filtered and concentrated in vacuo to afford ethyl 4-[hydroxy(1,3-thiazol-2-yl)methyl]cyclohexanecarboxylate as a 3:2 mixture of trans:cis isomers both of which are racemic mixtures. This brown oil was used directly in the subsequent step without further manipulation.

後処理

  1. temperaturethe solution cooled in an ice bath
  2. customdid not exceed 5° C.
  3. stirringwas stirred for 30 min
  4. customthen quenched by the addition of water and EtOAc
  5. customThe layers were separated
  6. dry with materialthe organic mixture dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9e494b057b444c0cb316ca3bbc0de01f
出典データセット
uspto-grants-2016_03
特許番号
US09290490B2

反応ノート

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