Triphenylphosphine → HCID 178498033, compound

HRID 1095147Notes

Reaction equation

HRID 1095147 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:27]([Si:31]([CH3:41])([CH3:40])[O:32][C@H:33]1[CH2:38][CH2:37][C@H:36](O)[CH2:35][CH2:34]1)([CH3:30])([CH3:29])[CH3:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:12][C@H:36]1[CH2:37][CH2:38][C@@H:33]([O:32][Si:31]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:40])[CH3:41])[CH2:34][CH2:35]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl esterHCID 178455371HCID 178455371, compound

Product 1

HCID 178498033HCID 178498033, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 5-chloro-2-hydroxybenzoate (2.07 g, 11 mmol) and diisopropyl azodicarboxylate (2.98 g, 14 mmol) (Aldrich) in anhydrous tetrahydrofuran (10 mL) at 0° C. was added a mixture of trans-4-(tert-buyl-dimethyl-silanyloxy)-cyclohexanol (3.2 g, 14 mmol) and triphenylphosphine (3.64 g, 14 mmol) in tetrahydrofuran (40 mL). The reaction mixture was stirred at room temperature for 18 h. The mixture was poured into water, extracted with ethyl acetate (3×). The organic layers were combined, washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (5% EtOAc;hexanes) to give cis-2-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-5-chloro-benzoic acid methyl ester as a yellow oil (Yield 4.0 g, 90%).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (5% EtOAc;hexanes)

Sources & evidence

ORD record
ord-c1446325c1fe49d1b66f0a0809f49b9d
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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