Triphenylphosphine → HCID 53706782, compound

HRID 704811Notes

Reaction equation

HRID 704811 reaction equation
[O:1]([C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[CH:16](O)[CH3:17])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24]([NH:26][O:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:25])([CH3:22])([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1.CCOCC>[C:19]([O:23][C:24]([N:26]([CH:16]([CH3:17])[CH:15]=[CH:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=1)[O:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamateHCID 5462977Diethyl azodicarboxylateHCID 20073356HCID 20073356, compound

Product 1

HCID 53706782HCID 53706782, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

(-)-(E)-1-3(-Phenoxyphenyl)but-1-en-3-ol from step (d) (2.6 g), N,O-bis(t-butoxycarbonyl)hydroxylamine (2.65 g), and triphenylphosphine (4.25 g) were taken up in toluene (30 ml) and cooled to -78° C. under N2. A solution of DEAD (2.9 g) in toluene (10 ml) was then added and the mixture allowed to warm to room tempterature. 40/60 pet.ether (60 ml) was added to precipitate Ph3P=O as a dark gummy mass. The mother liquor was decanted off and stripped to give a tan/orange oil which was eluted through a silica gel column using methylene chloride. The eluate was stripped to give a pale yellow oil which was eluted through a second silica gel column using ether/methylene chloride/40-60 pet.ether (1:1:8) and the eluate stripped to give the desired product as a colourless oil which was dried under high vacuum. Yield 1 97 g.

Workup

  1. temperatureto warm to room tempterature
  2. customto precipitate Ph3P=O as a dark gummy mass
  3. customThe mother liquor was decanted off
  4. customto give a tan/orange oil which
  5. washwas eluted through a silica gel column
  6. customto give a pale yellow oil which
  7. washwas eluted through a second silica gel column

Sources & evidence

ORD record
ord-c65425bc7b52499082c37597a90e0eec
Source dataset
uspto-grants-1991_01
Patent number
US04988733

Reaction notes

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