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

HRID 1816001Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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)+.

Workup

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

Sources & evidence

ORD record: ord-0b032ba556c94df7851ef9bada438bc2
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881736B1

Reaction notes

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