Phenol → HCID 14789659, compound

HRID 1886097Notes

Reaction equation

HRID 1886097 reaction equation
CN(C[C@@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C@H:6]1[OH:14])C.[C:15]1(O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[N:22]([C:29](OCC)=O)=NC(OCC)=O.O1CCC[CH2:35]1>>[O:14]([C@@H:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][C@H:5]1[N:22]([CH3:29])[CH3:35])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 996PhenolHCID 8028Tetrahydrofuran2×HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22845150HCID 22845150, compound

Product 1

HCID 14789659HCID 14789659, compound

Procedure

Stir a solution of TRANS-2,3-dihydro-2-dimethylamino methyl-inden-1-ol (7.65 g, 0.04 M) triphenylphosphine (11.54 g, 0.044 M), and phenol (4.14 g, 0.044 M) in 100 ml of tetrahydrofuran. Slowly add a solution of diethyl azodicarboxylate in 50 ml of tetrahydrofuran dropwise. Stir the mixture overnight and evaporate the solvent. Take up the residue in ether, filter insoluble material and reconcentrate. Chromatograph the residue on silica gel eluting with ether to yield two isomers, CIS and TRANS, with the CIS isomer eluting first.

Workup

  1. customevaporate the solvent
  2. filtrationfilter insoluble material and reconcentrate
  3. customChromatograph the residue on silica gel eluting with ether to yield two isomers, CIS
  4. washeluting first

Sources & evidence

ORD record
ord-e54fde7e00b444fabcba31c2e01a8436
Source dataset
uspto-grants-1992_09
Patent number
US05149714

Reaction notes

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