Potassium Hydroxide → 2-(7-Oxabicyclo[2.2.1]heptan-1-yl)propanoic acid

HRID 269743

반응식

HRID 269743 반응식
O[CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.C([O:11][C:12](=[O:23])[CH:13](P(OCC)(OCC)=O)[CH3:14])C.[H-].[Na+].[OH-].[K+]>C(O)C>[C:2]12([CH:13]([CH3:14])[C:12]([OH:23])=[O:11])[O:8][CH:5]([CH2:4][CH2:3]1)[CH2:6][CH2:7]2

참가 물질

6

반응물 4

HCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionateHCID 5437064-Hydroxycyclohexanone

생성물 1

HCID 693142162-(7-Oxabicyclo[2.2.1]heptan-1-yl)propanoic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The title compound was prepared by standard Wittig-Horner reaction from 4-hydroxy-cyclohexanone, 2-(diethoxy-phosphoryl)-propionic acid ethyl ester and sodium hydride (J. Boutagy, R. Thomas, Chem. Rev. 1974, 74, 87-99) and subsequent saponification with potassium hydroxide in ethanol. After recrystallization from n-heptane, the title compound was obtained as white solid. EI-MS: m/e=170(M+), 1H-NMR (90 MHz, CDCl3, TMS):δ 1.3 (d, J=8 Hz, 3H, Me), 1.7 (m, 8H, CH2), 3.0 (q, J=8 Hz, 1H, CH-Me), 4.6 (t, J=4.5 Hz, 1H, CH—O), 7.2 (s, 1H, COOH), mp 61-62° C., bp 120° C. (0.008 mbar).

후처리

  1. customAfter recrystallization from n-heptane

출처 및 근거

ORD 기록
ord-74b455d4ad484834b54da66cd62f9719
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449461B2

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