Triphenylphosphine → HCID 10098703, compound

HRID 458674Notes

Reaction equation

HRID 458674 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:31]=[C:30]([O:32][CH2:33][CH:34]=[C:35]([Cl:37])[Cl:36])[CH:29]=[C:28]([Cl:38])[C:22]=1[O:23][CH2:24][CH2:25][CH2:26][OH:27].[C:39]([O:43][C:44](=[O:53])[NH:45][C:46]1[CH:51]=[CH:50][C:49](O)=[CH:48][CH:47]=1)([CH3:42])([CH3:41])[CH3:40]>C1COCC1>[C:39]([O:43][C:44](=[O:53])[NH:45][C:46]1[CH:47]=[CH:48][C:49]([O:27][CH2:26][CH2:25][CH2:24][O:23][C:22]2[C:21]([Cl:20])=[CH:31][C:30]([O:32][CH2:33][CH:34]=[C:35]([Cl:37])[Cl:36])=[CH:29][C:28]=2[Cl:38])=[CH:50][CH:51]=1)([CH3:42])([CH3:40])[CH3:41]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 2756771N-Boc-4-hydroxyanilineHCID 113139803-[2,6-Dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propan-1-ol

Product 1

HCID 10098703HCID 10098703, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.69 g of azadicarboxylic acid diisopropyl ester are added dropwise at 0–5° C. to a solution of 1.97 g of triphenylphosphine in 60 ml of THF. After 30 minutes at 0–5° C., 2.5 g of 3-[2,6-dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propan-1-ol and 1.5 g of (4-hydroxy-phenyl)-carbamic acid tert-butyl ester dissolved in 30 ml of tetrahydrofuran are added dropwise. After being stirred for 24 hours at room temperature, the reaction mixture is concentrated and then purified over silica gel. (4-{3-[2,6-Dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propoxy}-phenyl)-carbamic acid tert-butyl ester (compound 1.6) is obtained.

Workup

  1. additionare added dropwise
  2. concentrationthe reaction mixture is concentrated
  3. custompurified over silica gel

Sources & evidence

ORD record
ord-efa59917209244d18a3a88d693e005e2
Source dataset
uspto-grants-2007_03
Patent number
US07192965B2

Reaction notes

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