Triphenylphosphine → HCID 67691041, compound

HRID 1078700Notes

Reaction equation

HRID 1078700 reaction equation
[O:1]([C@@H:9]1[C:14]2[CH:15]=[CH:16][C:17]([CH2:19][CH2:20][OH:21])=[CH:18][C:13]=2[O:12][CH2:11][C@H:10]1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:61]1[CH:62]=[C:63]([CH:69]=[CH:70][CH:71]=1)[C:64]([O:66][CH2:67][CH3:68])=[O:65]>O1CCCC1>[O:1]([C@@H:9]1[C:14]2[CH:15]=[CH:16][C:17]([CH2:19][CH2:20][O:21][C:70]3[CH:71]=[CH:61][CH:62]=[C:63]([C:64]([O:66][CH2:67][CH3:68])=[O:65])[CH:69]=3)=[CH:18][C:13]=2[O:12][CH2:11][C@H:10]1[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24522Ethyl 3-hydroxybenzoateHCID 5462977Diethyl azodicarboxylateHCID 676904902H-1-Benzopyran-7-ethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,4-dihydro-3-(phenylmethyl)-, trans-

Product 1

HCID 67691041HCID 67691041, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the compound of step A (720 mg, 18 mmole) in tetrahydrofuran (10 ml) was added diethylazodicarboxylate (430 μl, 2.5 mmole), triphenylphosphine (710 mg, 2.5 mmole) and ethyl 3-hydroxybenzoate (415 mg, 2.5 mmole). The mixture was refluxed for 3 days, the solvent removed in vacuo and the residue chromatographed (silica gel, 3:1 hexane:ether) to afford 258 mg of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 3 days
  2. customthe solvent removed in vacuo
  3. customthe residue chromatographed (silica gel, 3:1 hexane:ether)

Sources & evidence

ORD record
ord-39b77d7f0b1749be81a668f8a7d2e95b
Source dataset
uspto-grants-1996_08
Patent number
US05550152

Reaction notes

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