Hydrochloric Acid → 3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol

HRID 1037074노트

반응식

HRID 1037074 반응식
C(OCOC([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[B:16]1[O:20][C:19]([CH3:22])([CH3:21])C(C)(C)[O:17]1)(C)C)C.Cl>C1COCC1>[CH3:22][C:19]1([CH3:21])[O:20][B:16]([OH:17])[C:10]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]1=2

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 866855182-(2-(2-(Ethoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 866854553,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol수율 51.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of compound 2-(2-(2-(ethoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76.2 mmol) in THF (100 mL) was added 6 N HCl (381 mL). The reaction mixture was stirred at rt overnight, and the obtained mixture was extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (20:1) to give 3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (6.87 g; yield 51.2% over 2 steps) as a white solid. MS: m/z=177.1 (M+1, ESI+).

후처리

  1. extractionthe obtained mixture was extracted three times with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (20:1)

출처 및 근거

ORD 기록
ord-9190e62866e146bdae46ed8e5d66f050
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546357B2

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