Triphenylphosphine → HCID 86758464, compound

HRID 2304856Notes

Reaction equation

HRID 2304856 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:30][C:31]([F:59])([F:58])[C:32]([O:50][Si:51]([CH2:56][CH3:57])([CH2:54][CH3:55])[CH2:52][CH3:53])([C:46]([F:49])([F:48])[F:47])/[CH:33]=[CH:34]\[CH2:35][C:36]([CH3:45])([CH3:44])[CH2:37][CH2:38][CH2:39]/[CH:40]=[CH:41]/[CH2:42]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:59][C:31]([F:30])([F:58])[C:32]([O:50][Si:51]([CH2:56][CH3:57])([CH2:54][CH3:55])[CH2:52][CH3:53])([C:46]([F:48])([F:49])[F:47])/[CH:33]=[CH:34]\[CH2:35][C:36]([CH3:44])([CH3:45])[CH2:37][CH2:38][CH2:39]/[CH:40]=[CH:41]/[CH2:42][S:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 23245531HCID 23245531, compoundHCID 178418395HCID 178418395, compound

Product 1

HCID 86758464HCID 86758464, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6.59 g of 2-mercapto-benzothiazole and 7.87 g of triphenylphosphine in 65 ml of THF was added at 0° a solution of 9.25 g of (2E,9Z)-12,12,12-Trifluoro-7,7-dimethyl-11-triethylsilanyloxy-11-trifluoromethyl-dodeca-2,9-dien-1-ol in 35 ml of THF which was followed by addition of 8.09 g of diisopropyl azodicarboxylate over 20 min and stirring was continued at 0° for 1 h after which time t.l.c. indicated completion of the reaction. The mixture was washed with sat. aqueous NH4Cl- and NaCl-solution, the organic layer was dried over MgSO4 and evaporated. The residue was chromatographed on silica with hexane/AcOEt 9:1 to give 11.13 g of the pure (t.l.c.) title compound as a yellow oil. IR (neat): 1663w (C═C). MS (EI): 611/7 (M).

Workup

  1. customcompletion of the reaction
  2. washThe mixture was washed with sat. aqueous NH4Cl- and NaCl-solution
  3. dry with materialthe organic layer was dried over MgSO4
  4. customevaporated
  5. customThe residue was chromatographed on silica with hexane/AcOEt 9:1

Sources & evidence

ORD record
ord-4acc82e6ee954bca93ecf73f92a8498d
Source dataset
uspto-grants-2002_08
Patent number
US06437142B1

Reaction notes

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