Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → N-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide

HRID 1047070ノート

反応式

HRID 1047070 の反応式
C([CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([B:15]2[O:19][C:18]([CH3:21])([CH3:20])[C:17]([CH3:23])([CH3:22])[O:16]2)=[CH:11][CH:10]=1)=[O:7])(C)(C)C.[CH3:24]C(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>N1C=CC=CC=1.CCOC(C)=O>[CH3:24][N:8]([C:9]1[CH:14]=[CH:13][C:12]([B:15]2[O:16][C:17]([CH3:23])([CH3:22])[C:18]([CH3:21])([CH3:20])[O:19]2)=[CH:11][CH:10]=1)[C:6](=[O:7])[CH3:5]

参加物

5

反応物 2

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 67503416tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide

生成物 1

HCID 59232387N-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide収率 77%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide (100 mg, 0.429 mmol) in pyridine (1 mL) was added acetic anhydrate (1 mL) and stirred at room temperature for 23 hours. The mixture was diluted with AcOEt, washed with 1N HCl, brine, dried over Na2SO4, then filtrated through Celite pad. The filtrate was concentrated to afford the desired product (91 mg, 77%) as a dark brown solid. 1HNMR (CDCl3) 400 MHz δ: 7.85 (d, J=8.0 Hz, 2H), 7.19 (d, J=8.0 Hz, 2H), 3.27 (s, 3H), 1.88 (s, 3H), 1.35 (s, 12H).

後処理

  1. washwashed with 1N HCl, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltrated through Celite pad
  4. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-fdcb01d3dac143bd9504e13511b8feb8
出典データセット
uspto-grants-2013_10
特許番号
US08569331B2

反応ノート

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