Trifluoroacetic acid → 6-(2-azidopropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol

HRID 1037051ノート

反応式

HRID 1037051 の反応式
C(O)(C(F)(F)F)=O.O[C:9]([C:12]1[CH:13]=[CH:14][C:15]2[C:19]([CH3:21])([CH3:20])[O:18][B:17]([OH:22])[C:16]=2[CH:23]=1)([CH3:11])[CH3:10].[N-:24]=[N+:25]=[N-:26].[Na+]>C(Cl)(Cl)Cl>[N:24]([C:9]([C:12]1[CH:13]=[CH:14][C:15]2[C:19]([CH3:21])([CH3:20])[O:18][B:17]([OH:22])[C:16]=2[CH:23]=1)([CH3:11])[CH3:10])=[N+:25]=[N-:26]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 866854966-(2-hydroxypropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol

生成物 1

HCID 866854956-(2-azidopropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol収率 102%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

A solution of TFA (200 μL, 2 mmol) in chloroform (3 mL) was added slowly to a mixture of 6-(2-hydroxypropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol (88 mg, 0.4 mmol) and sodium azide (80 mg, 1.2 mmol) in chloroform (7 mL) at −5° C. to 0° C. The cooling bath was removed and the mixture was stirred at rt overnight. Concentrated ammonium hydroxide was added until pH was basic (moist PH paper). DCM (50 mL) was added and the organic layer was washed with brine:water (1:1), dried over Na2SO4, filtered and concentrated to give the crude product 6-(2-azidopropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol (100 mg) as colorless oil. It was used without further purification in the next step.

後処理

  1. customThe cooling bath was removed
  2. additionConcentrated ammonium hydroxide was added until pH
  3. additionDCM (50 mL) was added
  4. washthe organic layer was washed with brine:water (1:1)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-2130401305f74ed48c61154281de903d
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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