Toluene → HCID 178497284, compound

HRID 525469Notes

Reaction equation

HRID 525469 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=2)[CH2:6]1)=[O:4].[C:16]([C@H:20]1[CH2:25][CH2:24][C@H:23](O)[CH2:22][CH2:21]1)([CH3:19])([CH3:18])[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:16]([C@H:20]1[CH2:25][CH2:24][C@H:23]([O:15][C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:14][CH2:13]3)[CH2:22][CH2:21]1)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58055117Methyl 6-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylateHCID 178445812HCID 178445812, compound

Product 1

HCID 178497284HCID 178497284, compoundYield 16%

Procedure

To a mixture of 6-hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester (0.280 g, 1.36 mmol), trans-4-tert-butylcyclohexanol (0.2338 g, 1.496 mmol) and triphenylphosphine (0.7122 g, 2.715 mmol) in toluene (5 mL, 50 mmol) was stirred for 20 min, then, diisopropyl azodicarboxylate (0.34 mL, 1.6 mmol) was added dropwise at 0° C. The solution was stirred at reflux overnight. The reaction was added silica gel and the solvent was concentrated. The residue was purified with silica gel eluted with EtOAc in hexanes from 0 to 20% to give the product as a white precipitate (73 mg, 16%). LCMS Rt=1.50 min, m/z=450.10 [M+H].

Workup

  1. stirringThe solution was stirred
  2. temperatureat reflux overnight
  3. additionThe reaction was added silica gel
  4. concentrationthe solvent was concentrated
  5. customThe residue was purified with silica gel
  6. washeluted with EtOAc in hexanes from 0 to 20%

Sources & evidence

ORD record
ord-5deec096d9304bceb4f77dc270f8d9d2
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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