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

HRID 1394548

Reaction equation

HRID 1394548 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-6d0fa835ff6b4a0393ff26662fa4ca7e
Source dataset
uspto-grants-2008_03
Patent number
US07348456B2

Linked notes

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