Acetic Acid → 2,2-dimethyl-N-(4-octylphenyl)-1,3-dioxan-5-amine

HRID 2046032ノート

反応式

HRID 2046032 の反応式
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:16][C:17]1([CH3:24])[O:22][CH2:21][C:20](=O)[CH2:19][O:18]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl.CCOCC>[CH3:16][C:17]1([CH3:24])[O:22][CH2:21][CH:20]([NH:13][C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)[CH2:19][O:18]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 853464-OctylanilineHCID 27331412,2-Dimethyl-1,3-dioxan-5-oneHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 666148752,2-dimethyl-N-(4-octylphenyl)-1,3-dioxan-5-amine収率 63%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 3283Diethyl Ether溶媒

実験手順

To a mixture of 4-n-octylaniline (0.205 g; 1 mmol) and 2,2-dimethyl-1,3-dioxan-5-one (Helvetica Chimica Acta, 2003, 86, 2467; 0.13 g; 1 mmol) and NaBH(OAc)3 in 1,2 dichloroethane (3.5 ml), AcOH (0.06 ml; 1 mmol) was added and the mixture was stirred for 2 h at room temperature under N2, diluted to 20 ml with Et2O and washed with 1N NaOH, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified crystallization from hexane to give the title compound (0.2 g; 63%) as a colourless solid. 1H-NMR (CDCl3) 6.97 (d, 2H, J=8.4 Hz); 6.54 (d, 2H, J=8.4 Hz); 4.1 (dd, broad s, 3H, J=4.2, 11.9 Hz); 3.74 (dd, 2H, J=4.2, 11.9 Hz); 3.4 (m, 1H); 2.47 (t, 2H, J=7.91 Hz); 1.55 (m, 2H+H2O); 1.46 (s, 3H); 1.43 (s, 3H); 1.25 (m, 10H); 0.86 (m, 3H).

後処理

  1. additionwas added
  2. washwashed with 1N NaOH, H2O, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue was purified
  7. customcrystallization from hexane

出典と根拠

ORDレコード
ord-3bf10a0372c7416abe21267f7f985749
出典データセット
uspto-grants-2013_11
特許番号
US08592399B2

反応ノート

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