Ethyl cinnamyl carbonate → 1-Phenyl-1-phenoxy-2-propene

HRID 14440노트

반응식

HRID 14440 반응식
CC1(C)C(C=C[C:13]2[CH2:39][CH2:38][CH2:37]/[C:15](=[CH:16]/[CH:17]=[C:18]3/C(C)(C)C4C(N/3CCCCS(O)(=O)=O)=CC=CC=4)/[C:14]=2[O:40][C:41]2[CH:46]=[CH:45][C:44](OCCCCNCC3OC(O)C(N)C(O)C3O)=[CH:43][CH:42]=2)=[N+](CCCCS([O-])(=O)=O)C2C1=CC=CC=2.[O-]C1C=CC=CC=1.[Na+].C(=O)(OCC=CC1C=CC=CC=1)OCC>C1COCC1.[Cl-].[Na+].O>[C:15]1([CH:14]([O:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:13]=[CH2:39])[CH:16]=[CH:17][CH:18]=[CH:38][CH:37]=1

참가 물질

6

반응물 3

HCID 232463Ethyl cinnamyl carbonateHCID 4445035Phenolate SodiumHCID 178424610HCID 178424610, 화합물

생성물 1

HCID 117359621-Phenyl-1-phenoxy-2-propene수율 75%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

[(COD)Ir(κ2-L1)(L1)] (Ir-2) (13.8 mg, 0.0100 mmol), [(COD)IrCl]2 (3.4 mg, 0.0050 mmol) and sodium phenoxide (232 mg, 2.00 mmol) were dissolved in 1.0 mL of THF. Ethyl cinnamyl carbonate (192 mg, 0.930 mmol) was added to the reaction mixture by syringe. After being stirred at room temperature for 2 h, the reaction mixture was poured into brine, extracted with ether, dried, filtered, and concentrated. 1H NMR analysis of the mixture indicated that the ratio of branched to linear regioisomers was 95/5. The residue was purified by flash chromatography on silica gel (1% Et2O/Hexanes) to afford 157 mg (75%) of 1-phenyl-1-phenoxy-2-propene as a viscous oil. [Rf 0.85 (5% Et2O/Hexanes)] HPLC analysis indicated an enantiomeric excess of 94% [Chiralcel® OJ-H column, eluting with 99.75/0.25 hexane/i-PrOH, 0.6 mL/min, 220 nm; major enantiomer TR, 45.4, minor enantiomer TR 55.3 min]; [α]D20=+8.9 (c 1.4, CHCl3); 1H NMR (500.13 MHz, CDCl3) δ 7.48-7.27 (m, 8H), 7.01-6.96 (m, 2H), 6.15 (ddd, J=17.2, 10.4, 5.9 Hz, 1H), 5.70 (d, J=5.9 Hz, 1H), 5.41 (d, J=17.2 Hz, 1H), 5.31 (d, J=10.4 Hz, 1H). 13C NMR (125.7 MHz, CDCl3) δ 157.9 (C), 140.1 (C), 137.9 (CH), 129.3 (CH), 128.6 (CH), 127.8 (CH), 126.6 (CH), 121.0 (CH), 116.5 (CH2), 116.2 (CH), 80.8 (CH).

후처리

  1. extractionextracted with ether
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (1% Et2O/Hexanes)

출처 및 근거

ORD 기록
ord-787d893ae1a94fe2867eace2a9f53ac9
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732365B2

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