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

HRID 928101노트

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HRID 928101 반응식
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

참가 물질

5

반응물 3

HCID 9256ThiazoleHCID 13548164(1R,4R)-Ethyl 4-formylcyclohexanecarboxylateHCID 178461733HCID 178461733, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e494b057b444c0cb316ca3bbc0de01f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290490B2

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