Phthalimide → HCID 13958749, compound

HRID 255917Notes

Reaction equation

HRID 255917 reaction equation
[CH3:1]/[C:2](=[CH:5]\[F:6])/[CH2:3]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:38]1(=[O:48])[NH:42][C:41](=[O:43])[C:40]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:39]12>C1COCC1>[C:38]1(=[O:48])[N:42]([CH2:1]/[C:2](/[CH3:3])=[CH:5]/[F:6])[C:41](=[O:43])[C:40]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:39]12

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13958748(E)-2-methyl-3-fluoroallyl alcohol

Product 1

HCID 13958749HCID 13958749, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-2-methyl-3-fluoroallyl alcohol (prepared in Step D) (17.11 g), triphenylphosphine (49.80 g), diethyl azodicarboxylate (33.06 g) and phthalimide (27.93 g) in THF (500 ml) is stirred at room temperature overnight. The THF is evaporated and the oily residue is extracted three times with hexane giving a powdery solid which is subsequently extracted three times with ether. The combined extracts are evaporated and the residue (63 g) is purified by chromatography on silica gel (950 g) using a mixture of 20% diethyl ether/light petroleum. The major fraction is a colorless crystalline mass (28.6 g, 69% yield) which is essentially pure product. A small portion can be crystallized from hexane to give (E)-1-phthalimido-2-methyl-3-fluoro-2-propene as colorless plates: m.p. 57°-58° C.

Workup

  1. customThe THF is evaporated
  2. extractionthe oily residue is extracted three times with hexane giving a powdery solid which
  3. extractionis subsequently extracted three times with ether
  4. customThe combined extracts are evaporated
  5. customthe residue (63 g) is purified by chromatography on silica gel (950 g)
  6. additiona mixture of 20% diethyl ether/light petroleum
  7. customA small portion can be crystallized from hexane

Sources & evidence

ORD record
ord-a638013f18094c6283913f9e9562083b
Source dataset
uspto-grants-1987_10
Patent number
US04699928

Reaction notes

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