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

HRID 1816001ノート

反応式

HRID 1816001 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6343Ethanethiol溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-0b032ba556c94df7851ef9bada438bc2
出典データセット
uspto-grants-2005_04
特許番号
US06881736B1

反応ノート

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