Triphenylphosphine → HCID 54494149, compound

HRID 377577Notes

Reaction equation

HRID 377577 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20]N1C(=O)CCC1=O.O[CH2:29][C:30]1[O:35][CH2:34][N:33]([C:36]([CH3:45])([CH3:44])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:32](=[O:46])[C:31]=1[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>O1CCCC1>[Cl:20][CH2:29][C:30]1[O:35][CH2:34][N:33]([C:36]([CH3:45])([CH3:44])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:32](=[O:46])[C:31]=1[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 57067707HCID 57067707, compound

Product 1

HCID 54494149HCID 54494149, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of triphenylphosphine (1.82 g) in tetrahydrofuran was added dropwise to a stirred solution of N-chlorosuccinimide (1.08 g) in tetrahydrofuran. After 10 minutes a solution of tert butyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (2.0 g) in tetrahydrofuran was added. The mixture was stirred overnight and partitioned between ether and water, and the organic phase washed (brine), dried (magnesium sulphate) and evaporated. The residue was purified by dry column chromatography on silica gel, eluting with dichloromethanelhexane (2:1) to give tert butyl 2-(6-chloromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (1.49 g) as a white solid, m.p. 128-129° C.

Workup

  1. custompartitioned between ether and water
  2. washthe organic phase washed (brine)
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated
  5. customThe residue was purified
  6. customby dry column chromatography on silica gel
  7. washeluting with dichloromethanelhexane (2:1)

Sources & evidence

ORD record
ord-44ad367ee7834e29bc9511c8560839ba
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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