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

HRID 1020784

반응식

HRID 1020784 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-56a1b6da687c4867a7bb0d3aa7aa6186
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716478B2

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