Tetrahydrofuran → Benzoic acid, 4-hexyl-, methyl ester

HRID 1795377

반응식

HRID 1795377 반응식
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][CH:5]=1.C1COCC1.CN1CCCC1=O.[CH2:31]([Mg]Br)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CCOCC>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 13387N-methyl-2-pyrrolidoneHCID 5315090Methyl 4-(((trifluoromethyl)sulfonyl)oxy)benzoateHCID 178444609HCID 178444609, 화합물

생성물 1

HCID 591633Benzoic acid, 4-hexyl-, methyl ester수율 93%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A flame-dried two-necked flask is charged under argon with 4-(trifluoromethylsulfonyloxy)benzoic acid methyl ester (760 mg, 2.66 mmol), Fe(acac)3 (47 mg, 0.13 mmol), THF (30 mL) and N-methylpyrrolidone (NMP, 1.7 mL). A solution of n-hexylmagnesium bromide (2M in Et2O, 1.7 mL, 3.4 mmol) is added via syringe to the resulting red solution, causing an immediate color change to dark brown and finally to violet. The resulting mixture is stirred for 5 min, the reaction is diluted with Et2O and is carefully quenched upon addition of aq. HCl (1M, ca. 10 mL). Work-up followed by flash chromatography of the crude product as described above provides 4-hexylbenzoic acid methyl ester as a colorless syrup (540 mg, 93%). The spectroscopic and analytical data are identical to those compiled above.

후처리

  1. customis carefully quenched upon addition of aq. HCl (1M, ca. 10 mL)

출처 및 근거

ORD 기록
ord-247077bc74b74d10a2c4b0718a7f4454
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026478B2

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