Trifluoroacetic acid → HCID 18426311, compound

HRID 1871283Notes

Reaction equation

HRID 1871283 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:40]=[CH:39][CH:38]=[CH:37][C:8]=2[C:9]=1[C:10]([C:12]1[CH:13]=[C:14]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:15]([O:24]COCCOC)=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=1)=[O:11])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)Cl.CCOCC>[CH2:1]([C:5]1[O:6][C:7]2[CH:40]=[CH:39][CH:38]=[CH:37][C:8]=2[C:9]=1[C:10]([C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([OH:24])=[C:14]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:13]=1)=[O:11])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23445658HCID 23445658, compound

Product 1

HCID 18426311HCID 18426311, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

At ambient temperature, to a stirred solution of (2-n-butyl-benzofuran-3-yl)-(2'-[(2-methoxyethoxy)methoxy]-[1,1';3',1"]terphenyl-5'-yl)-methanone (0.371 g, 0.695 mmol) in CH2Cl2 (3.71 mL) was added trifluoroacetic acid (3.71 mL). After 0.5 h, the reaction was diluted with ether (50 mL), washed with H2O (3×), dried (MgSO4) and concentrated. The crude product was purified on Biotage KP-Sil eluting with 10% acetone/hexane to give 0.281 g (90%) of the title compound. 1H NMR (DMSO-d6) δ 0.77 (t, 3 H), 1.22 (sextet, 2 H), 1.64 (quintet, 2 H), 2.87 (t, 2 H), 7.29-7.65 (m, 14 H), 7.66 (s, 2 H), 9.39 (s, 1 H).

Workup

  1. washwashed with H2O (3×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was purified on Biotage
  5. washKP-Sil eluting with 10% acetone/hexane

Sources & evidence

ORD record
ord-7cf3a8e6375f45aa8d22c8d28340499c
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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