Triphenylphosphine → HCID 178498034, compound

HRID 1095150Notes

Reaction equation

HRID 1095150 reaction equation
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:18]=[CH:19][C:20](O)=[C:21]([CH:26]=1)[C:22]([O:24][CH3:25])=[O:23].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:25][O:24][C:22](=[O:23])[C:21]1[CH:26]=[C:17]([Cl:16])[CH:18]=[CH:19][C:20]=1[O:13][C@H:10]1[CH2:9][CH2:8][C@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:15])[CH3:14])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl esterHCID 178455370HCID 178455370, compound

Product 1

HCID 178498034HCID 178498034, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in example 94b, cis-4-(tert-buyl-dimethyl-silanyloxy)-cyclohexanol (2.7 g, 12 mmol) was reacted with methyl 5-chloro-2-hydroxybenzoate (1.77 g, 9.5 mmol) and diisopropyl azodicarboxylate, triphenylphosphine in tetrahydrofuran to give trans-2-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-5-chloro-benzoic acid methyl ester as a yellow oil (Yield 2.7 g, 71%).

Sources & evidence

ORD record
ord-e02449977ded4203866e40250ed337ce
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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