Hydrochloric Acid → 1,3-Dihydro-1-hydroxy-2,1-benzoxaborol-5-ol

HRID 2284469ノート

反応式

HRID 2284469 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([B:10]2[O:14][C:13](C)(C)C(C)(C)[O:11]2)=[C:6]([CH:9]=1)C=O.[BH4-].[Na+].O.Cl>CO>[B:10]1([OH:11])[C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:9][C:6]=2[CH2:13][O:14]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 576899875-Hydroxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

生成物 1

HCID 579686991,3-Dihydro-1-hydroxy-2,1-benzoxaborol-5-ol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 5-hydroxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (5.5 g, 22 mmol, 1.0 equiv) in methanol (25 mL). This was followed by the addition of NaBH4 (1.24 g, 32.6 mmol, 1.5 equiv) in several batches at 0° C. The resulting solution was stirred for 10 min at 0° C., then it was concentrated under vacuum to get rid of half methanol at low temperature. To the residual solution was added water (6 mL) and HCl (6M, 14.5 mL) dropwise at 0° C. The resulting solution was stirred overnight at room temperature. Then it was concentrated under vacuum at low temperature to remove MeOH. The solid was collected by filtration. This resulted in 2.0 g of benzo[c][1,2]oxaborole-1,5(3H)-diol as a white solid.

後処理

  1. customInto a 100-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationit was concentrated under vacuum
  4. customto get rid of half methanol at low temperature
  5. stirringThe resulting solution was stirred overnight at room temperature
  6. concentrationThen it was concentrated under vacuum at low temperature
  7. customto remove MeOH
  8. filtrationThe solid was collected by filtration
  9. customThis resulted in 2.0 g of benzo[c][1,2]oxaborole-1,5(3H)-diol as a white solid

出典と根拠

ORDレコード
ord-17938e693da34a6c993d369cd2a14a95
出典データセット
uspto-grants-2015_09
特許番号
US09145429B2

反応ノート

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