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

HRID 1037074ノート

反応式

HRID 1037074 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-9190e62866e146bdae46ed8e5d66f050
出典データセット
uspto-grants-2013_10
特許番号
US08546357B2

反応ノート

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