Phenol → HCID 178454065, compound

HRID 1913529Notes

Reaction equation

HRID 1913529 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([OH:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:16]1(O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.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>O1CCCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([O:14][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178418813HCID 178418813, compound

Product 1

HCID 178454065HCID 178454065, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl(cis-4-hydroxycyclohexyl)carbamate (2.00 g), phenol (1.14 g), and triphenylphosphine (3.17 g) were dissolved in tetrahydrofuran (40.0 mL). Then, to the solution, diisopropyl azodicarboxylate (6.49 mL) was added dropwise at room temperature, and the mixture was stirred at room temperature for 63 hours. The reaction solution was concentrated and then purified by silica gel column chromatography (eluting solvent: hexane-hexane/ethyl acetate-90/10) to obtain the title compound (1.80 g).

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified by silica gel column chromatography (eluting solvent: hexane-hexane/ethyl acetate-90/10)

Sources & evidence

ORD record
ord-1de8a0eb813a4ede8c6e15de2fd4fba8
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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