Water → Methyl 2-(3-benzyl-2-thienyl)-3-methoxypropenoate

HRID 256554

반응식

HRID 256554 반응식
C[C:2](C)([O-:4])C.[K+].[Cl-].COC[P+]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(C1C=CC=CC=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O([CH2:37][C:38]1[CH:42]=[CH:41][S:40][C:39]=1[C:43](=[O:48])[C:44]([O:46][CH3:47])=[O:45])C1C=CC=CC=1.[OH2:49].[CH2:50]1[CH2:54][O:53][CH2:52][CH2:51]1>CCOCC>[C:43]([C:39]1[S:40][CH:41]=[C:42](/[C:50](=[CH:51]\[O:4][CH3:2])/[C:54]([O:53][CH3:52])=[O:49])[CH:38]=1)(=[O:48])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1.[CH2:37]([C:38]1[CH:42]=[CH:41][S:40][C:39]=1[C:43](=[CH:52][O:53][CH3:54])[C:44]([O:46][CH3:47])=[O:45])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

8

반응물 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 14326170HCID 14326170, 화합물HCID 23665647Potassium tert-butoxide

생성물 2

HCID 54504656Methyl 2-(3-benzyl-2-thienyl)-3-methoxypropenoateHCID 67883648HCID 67883648, 화합물

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Potassium tert-butoxide (844 mg) was added in one portion to a stirred suspension of (methoxymethyl)triphenylphosphonium chloride (2.86 g) in ether (30 ml). The reaction mixture became red. After 20 minutes, a solution of methyl 2-(3-phenoxymethyl-2-thienyl)-2-oxoacetate (770 mg) in THF (10 ml) was added in one portion and the red colour was discharged. The resulting mixture was stirred at room temperature for 30 minutes then poured into water. The organic and aqueous layers were separated, and the latter was extracted with ether. The combined organic layers were washed with water, dried, concentrated and chromatographed using a 1:1 mixture of ether and petrol as eluent to give (i) the (Z)-isomer of the title compound (230 mg, 27%) as a pale yellow oil, IR (film) 1710, 1625 cm-1, 1H nmr: see Table VII; and (ii) the (E)-isomer of the title compound (80 mg, 9% yield), also a pale yellow oil, IR (film) 1700, 1620 cm-1, 1H nmr: see Table VII.

후처리

  1. customThe organic and aqueous layers were separated
  2. extractionthe latter was extracted with ether
  3. washThe combined organic layers were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed
  7. additiona 1:1 mixture of ether and petrol as eluent

출처 및 근거

ORD 기록
ord-f2e71cca8ec84064bb603526505f08e0
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258360

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