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 1047070노트

반응식

HRID 1047070 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-fdcb01d3dac143bd9504e13511b8feb8
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569331B2

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