Boron trifluoride etherate → 3-Cyclopentyl-2-methoxy-3-oxo-propionic acid methyl ester

HRID 1020771노트

반응식

HRID 1020771 반응식
[C:1](O)(=[O:3])C.C(O)(=O)C.I(C1C=CC=CC=1)=O.B(F)(F)F.CCOCC.[CH2:26]([O:28][C:29](=[O:38])[CH2:30][C:31]([CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:32])C>CO>[CH3:26][O:28][C:29](=[O:38])[CH:30]([O:3][CH3:1])[C:31]([CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:32]

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 11159709Ethyl 3-cyclopentyl-3-oxopropanoateHCID 73357407Acetic acid;iodosylbenzene

생성물 1

HCID 597772863-Cyclopentyl-2-methoxy-3-oxo-propionic acid methyl ester

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

The title compound was prepared using a method analogous to that described in Tetrahedron 1998, 44, 1603-1607: To a suspension of iodosobenzene diacetate (5.2 g, 16.3 mmol) in MeOH (40 mL) was added BF3.OEt2 (2.1 mL, 16.3 mmol). The resulting mixture was added to 3-cyclopentyl-3-oxo-propionic acid ethyl ester (3.0 g, 16.3 mmol) and stirred at rt overnight. The mixture was concentrated to half the total volume, quenched with satd. aq. NaHCO3, and extracted with CHCl3 (2×). The combined organic layers were dried and concentrated and the crude residue purified (EtOAc/hexanes) to yield a colorless oil (1.5 g, 43%). 1H NMR (MeOD): 4.4 (s, 1H), 3.8 (s, 3H), 3.5 (s, 3H), 3.3-3.2 (m, 1H), 1.9-1.5 (m, 8H).

후처리

  1. concentrationThe mixture was concentrated to half the total volume
  2. customquenched with satd
  3. extractionaq. NaHCO3, and extracted with CHCl3 (2×)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customthe crude residue purified (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-71aa842dc4ad41758ec274798e6610fe
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716475B2

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