2-Phenylethanol → HCID 69309435, compound

HRID 269546Notes

Reaction equation

HRID 269546 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[OH:25])=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].[CH2:26](O)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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>C1COCC1.O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[O:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 60542-PhenylethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58730988HCID 58730988, compound

Product 1

HCID 69309435HCID 69309435, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-chloro-2-hydroxy-[1,1′;2′,1″]terphenyl-3″-carboxylic acid ethyl ester (100 mg, 0.28 mmol), phenethyl alcohol (31 mg, 0.25 mmol), triphenyl phosphine (74 mg, 0.28 mmol), diisopropyl azodicarboxylate (57 mg, 0.28 mmol) in THF (6 ml) was stirred at room temperature overnight. The mixture was then poured into water and extracted with ether, the organic layers were dried over MgSO4 and evaporated. The residue was chromatographed through an SPE column using iso-hexane to yield the title compound (95 mg, 80%) as an oil.

Workup

  1. extractionextracted with ether
  2. dry with materialthe organic layers were dried over MgSO4
  3. customevaporated
  4. customThe residue was chromatographed through an SPE column

Sources & evidence

ORD record
ord-c5d9e93173ad49b5a373b7b805e488b6
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

Loading…