Ethyl orthoformate → HCID 59770553, compound

HRID 2218710Notes

Reaction equation

HRID 2218710 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH:8]=[C:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][CH2:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)[CH:5]=[CH:4][C:3]=1[OH:24].[CH2:25](OC(OCC)OCC)C>>[CH:19]1[C:14]2[CH2:13][CH2:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]=3[C:9](=[CH:8][C:6]3[CH:5]=[CH:4][C:3]4[O:24][CH:25]=[N:1][C:2]=4[CH:7]=3)[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 59770511HCID 59770511, compound

Product 1

HCID 59770553HCID 59770553, compoundYield 84%

Procedure

Dissolve 2-amino-4-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenol (see Example 63) (60 mg, 0.191 mmol) in triethylorthoformate (3 mL) and heat to reflux for 4.5 h. Cool to room temperature and concentrate in-vacuo to a brown oil. Chromatograph on 10 g silica gel eluting with 5% to 25% ethyl acetate/hexanes to afford 52 mg (84%) of the title compound as a colorless oil; MS (ES) 324 (M+H), 322 (M−H), HPLC shows 94% purity.

Workup

  1. temperatureheat
  2. temperatureto reflux for 4.5 h
  3. concentrationconcentrate in-vacuo to a brown oil

Sources & evidence

ORD record
ord-aa363906948f45f1a5c0cd82d0881ac2
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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