4-tert-Butylcyclohexanol → HCID 178422868, compound

HRID 2404171Notes

Reaction equation

HRID 2404171 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.[C:13]([CH:17]1[CH2:22][CH2:21][CH:20](O)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:13]([C@H:17]1[CH2:22][CH2:21][C@H:20]([O:12][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]3)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 5

HCID 73914-tert-ButylcyclohexanolHCID 8028Tetrahydrofuran2×HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5943956-Hydroxy-2-methylquinoline

Product 1

HCID 178422868HCID 178422868, compoundYield 56%

Procedure

To a solution of 2-Methyl-quinolin-6-ol (4.13 g, 0.0259 mol), c is 4-tert-Butyl-cyclohexanol (4.86 g, 0.0311 mol) and triphenylphosphine (9.53 g, 0.0363 mol; Supplier=Aldrich) in tetrahydrofuran (100 mL, 1 mol; Supplier=Acros), cooled in an ice bath, was added diisopropyl azodicarboxylate (7.61 mL, 0.0363 mol; Supplier=Acros) in Tetrahydrofuran (10 mL, 0.1 mol; Supplier=Acros). The reaction mixture was stirred for 72 h allowing to reach room temperature. The solvent was removed under reduced pressure and the residue was taken up in methylene chloride, adsorbed onto silica gel and purified by flash chromatography (0-30% ethyl acetate in hexanes) to give the title compound in 56% yield. ESI-MS (M+H+): 298.3.

Workup

  1. temperaturecooled in an ice bath
  2. customto reach room temperature
  3. customThe solvent was removed under reduced pressure
  4. custompurified by flash chromatography (0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a88a55e1951a4c48b04c67ee84168a78
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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