Cesium carbonate → 6-(3-Methoxy-phenyl)-hex-5-ynoic acid methyl ester

HRID 227925

반응식

HRID 227925 반응식
Cl[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:10]([OH:17])(=[O:16])[CH2:11][CH2:12][CH2:13][C:14]#[CH:15].[CH:18]1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(S([O-])(=O)=O)=CC=2C(C)C)CCCCC1.[Na+].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C.O>[CH3:18][O:16][C:10](=[O:17])[CH2:11][CH2:12][CH2:13][C:14]#[C:15][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 178333-ChloroanisoleHCID 1430365-Hexynoic acidHCID 23674066Sodium 2'-(dicyclohexylphosphino)-2,6-diisopropyl-[1,1'-biphenyl]-4-sulfonate

생성물 1

HCID 115938296-(3-Methoxy-phenyl)-hex-5-ynoic acid methyl ester수율 688.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

The general procedure described in Example 27 was used with 3-chloroanisole (0.061 mL, 0.50 mmol), 5-hexynoic acid (0.072 mL, 0.65 mmol), PdCl2(CH3CN)2 (3.2 mg, 0.0125 mmol, 1.25 mol %), sodium 2′-(dicyclohexyl-phosphanyl)-2,6-diisopropyl-biphenyl-4-sulfonate (20.0 mg, 0.0375 mmol, 3.75 mol %), Cs2CO3 (650 mg, 2.00 mmol), water (1.0 mL), acetonitrile (1.0 mL), 10 h, 100° C. The product was isolated as a colorless oil (60 mg, 85%). 1H NMR (400 MHz, CDCl3) δ: 7.16 (t, 1H, J=8.0 Hz), 6.96 (dt, 1H, J=1.2 Hz, 7.6 Hz), 6.89 (m, 1H), 6.80 (qd, 1H, J=1.2 Hz, 2.4 Hz, 8.4 Hz), 3.76 (s, 3H), 3.66 (s, 3H), 2.48 (t, 2H, J=7.2 Hz), 2.45 (t, 2H, J=6.8 Hz), 1.90 (q, 2H, J=6.8 Hz). 13C NMR (125 MHz, CDCl3) δ: 173.8, 159.4, 129.5, 124.9, 124.3, 116.6, 114.5, 88.9, 81.6, 55.4, 51.8, 33.1, 24.1, 19.1. IR (neat, cm−1): 2952, 2232, 1737, 1598, 1574, 1481, 1434, 1316, 1287, 1206, 1164, 1045, 854, 786, 688. 1H NMR (CDCl3) is shown in FIG. 8.

출처 및 근거

ORD 기록
ord-13af8e4ac64c43859b2c7d48a545f6e0
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560596B2

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