Triphenylphosphine → Benzyl 2-[(pyridin-2-yl)oxy]propanoate

HRID 1394548

반응식

HRID 1394548 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:12])[CH:9]([CH3:11])O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl.CCCCCC>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH:9]([CH3:11])[C:8]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 98054Benzyl lactateHCID 5462977Diethyl azodicarboxylateHCID 178516071HCID 178516071, 화합물

생성물 1

HCID 16098326Benzyl 2-[(pyridin-2-yl)oxy]propanoate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

To a mixture of 2-hydroxypyridine (2.9 g, 30 mmol), benzyl lactate (5.0 g, 21 mmol) and triphenylphosphine (12 g, 47 mmol) in 100 mL of methylene chloride was added diethylazodicarboxylate (7.8 mL, 45 mmol) at 0° C. The reaction was allowed to warm to room temperature for 4 h. The resulting mixture was diluted with hexane (100 mL) and concentrated with 20 g of silica gel. The material was loaded onto a silica gel column, which was eluted with 10% ethyl acetate in hexane to give the title compound. 1H NMR (500 MHz, CD3OD): δ 8.00 (dd, 1H), 7.68 (ddd, 1H), 7.36-7.28 (m, 5 H), 6.94 (dd, 1H), 6.84 (dd, 1H), 5.30 (q, 1H), 5.18 (s, 2H), 1.59 (d, 3H). LC-MS: m/e 258 (M+H)+ (3.3 min).

후처리

  1. concentrationconcentrated with 20 g of silica gel
  2. washwas eluted with 10% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-6d0fa835ff6b4a0393ff26662fa4ca7e
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348456B2

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