Triphenylphosphine → HCID 89964578, compound

HRID 1846227Notes

Reaction equation

HRID 1846227 reaction equation
BrC1C([O:8][CH2:9][CH2:10][CH2:11][CH:12]=C)=CC=CN=1.N(C(OCC)=O)=N[C:16](OCC)=O.Br[C:27]1[C:32]([OH:33])=[CH:31][CH:30]=[CH:29][N:28]=1.C(O)C[CH2:36][CH:37]=[CH2:38].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.C([O-])(O)=O.[Na+]>[C:37]([C:29]1[N:28]=[C:27]2[C:9](=[O:8])[CH2:10][CH2:11][CH2:12][O:33][C:32]2=[CH:31][CH:30]=1)([CH3:36])([CH3:38])[CH3:16]

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 131814-Penten-1-OLHCID 230702-Bromo-3-pyridinolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 64982982HCID 64982982, compound

Product 1

HCID 89964578HCID 89964578, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

2-bromo-3-(pent-4-en-1-yloxy)pyridine. Diethyl azodicarboxylate (1 eq.) is added dropwise to a stirring mixture of 2-bromo-3-hydroxypyridine (0.92 eq,), pent-4-en-1-ol (0.92 eq), and PPh3 (1.1 eq) in THF (0.2 M) at 0° C. under a N2 atmosphere. The reaction mixture is warmed to 50° C. in an oil bath. Reaction progress is monitored by TLC until judged complete. The reaction mixture is cooled to ambient temperature and diluted with saturated NaHCO3 solution. The aqueous solution is extracted with EtOAc, and the organic layer is dried over Na2SO4 and concentrated. The compound that may be thus obtained is purified by column chromatography to afford the title compound.

Workup

  1. customReaction progress
  2. temperatureThe reaction mixture is cooled to ambient temperature
  3. extractionThe aqueous solution is extracted with EtOAc
  4. dry with materialthe organic layer is dried over Na2SO4
  5. concentrationconcentrated
  6. customThe compound that may be thus obtained
  7. customis purified by column chromatography

Sources & evidence

ORD record
ord-a244e876f5da4ad3906c34304d0f9f91
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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