Triphenylphosphine → HCID 68572431, compound

HRID 747626Notes

Reaction equation

HRID 747626 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Si:34]([O:41][CH2:42][CH2:43][CH2:44]O)([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35].[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([NH:53][S:54]([C:57]2[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[C:59]([O:65][CH3:66])[CH:58]=2)(=[O:56])=[O:55])=[C:49]([CH2:67][C:68]2[C:73]([F:74])=[CH:72][CH:71]=[CH:70][C:69]=2[F:75])[CH:48]=1>O1CCCC1>[C:37]([Si:34]([CH3:35])([CH3:36])[O:41][CH2:42][CH2:43][CH2:44][N:53]([C:50]1[CH:51]=[CH:52][C:47]([Cl:46])=[CH:48][C:49]=1[CH2:67][C:68]1[C:73]([F:74])=[CH:72][CH:71]=[CH:70][C:69]=1[F:75])[S:54]([C:57]1[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[C:59]([O:65][CH3:66])[CH:58]=1)(=[O:56])=[O:55])([CH3:38])([CH3:39])[CH3:40]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-olHCID 68564783HCID 68564783, compound

Product 1

HCID 68572431HCID 68572431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 4.3 g of triphenylphosphine in 20 ml of tetrahydrofuran are added, at room temperature, 3.25 ml of diisopropyl azodicarboxylate. After 30 minutes, 3.5 ml of 3-[tert-butyl(dimethyl)silyloxy]propanol dissolved in 30 ml of tetrahydrofuran are introduced. The mixture is left at room temperature for 30 minutes, and 5 g of N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-3,4-dimethoxybenzenesulfonamide are then introduced. After 48 hours at room temperature, the reaction medium is concentrated and then chromatographed on a column of silica gel to give 8.09 g of the expected product.

Workup

  1. additionare introduced
  2. waitThe mixture is left at room temperature for 30 minutes
  3. waitAfter 48 hours at room temperature
  4. concentrationthe reaction medium is concentrated
  5. customchromatographed on a column of silica gel

Sources & evidence

ORD record
ord-c44db9d4080049579d4729838f6f4e6d
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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