Boron trifluoride etherate → Methyl I(2)-[(4-hydroxyphenyl)methyl]-5-methyl-2-thiazolepropanoate

HRID 1816001노트

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HRID 1816001 반응식
[CH3:1][C:2]1[S:6][C:5]([CH:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]CC3C=CC=CC=3)=[CH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:4][CH:3]=1.B(F)(F)F.CCOCC>CCS>[CH3:1][C:2]1[S:6][C:5]([CH:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:4][CH:3]=1

참가 물질

4

반응물 2

HCID 8000Boron trifluoride etherateHCID 86759662Methyl (+/-)-3-(5-methylthiazol-2-yl)-4-(4-benzyloxyphenyl)butanoate

생성물 1

HCID 20775669Methyl I(2)-[(4-hydroxyphenyl)methyl]-5-methyl-2-thiazolepropanoate수율 86.3%

시약·촉매·용매 1

HCID 6343Ethanethiol용매

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온도
0 °C

실험 절차

To a solution of methyl (±)-3-(5-methylthiazol-2-yl)-4-(4-benzyloxyphenyl)butanoate (0.99 mmole, crude) in EtSH (5 mL) at RT was added BF3 OEt2 (0.6 mL). After 18 hr. additional BF3.OEt2 (0.6 mL) was added. After another 18 hr, the mixture was cooled to 0° C. and carefully quenched with saturated NaHCO3. The resulting mixture was extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel (50% EtOAc/hexanes) to give the title compound (249 mg, 86% over 3 steps) as a yellow solid: MS (ES) m/e 292 (M+H)+.

후처리

  1. waitAfter another 18 hr
  2. customcarefully quenched with saturated NaHCO3
  3. extractionThe resulting mixture was extracted with CH2Cl2 (3×25 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-0b032ba556c94df7851ef9bada438bc2
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06881736B1

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