Sodium borohydride → [4-(Azidomethyl)phenyl]methanol

HRID 1509360노트

반응식

HRID 1509360 반응식
[N:1]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[BH4-].[Na+]>CO.C(OCC)(=O)C>[N:1]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1)=[N+:2]=[N-:3]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 574448534-(Azidomethyl)benzaldehyde

생성물 1

HCID 23132430[4-(Azidomethyl)phenyl]methanol수율 97%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

Azide 4 (2.0 g, 12.4 mmol) was dissolved in MeOH (50 ml) and cooled to 0° C. before NaBH4 was added slowly and the reaction mixture was stirred for 1 hour, after which the solvent was evaporated. The residue obtained was dissolved in ethyl acetate (50 ml) and water (50 ml), the phases were separated and the organic phase was washed with water (100 ml), dried over Na2SO4, and evaporated to yield 5 as a clear oil (1.96 g, 12.0 mmol, 97%). Rf=0.45 (DCM); νmax=cm−1; 1H NMR (300 MHz, CDCl3) δ=7.40 (d, 3J(H,H) 8.2 Hz, 2H, ArCH α to CH2OH), 7.33 (d, 3J(H,H)=8.2 Hz, 2H, ArCH α to CH2N3), 4.71 (s, 2H, CH2OH), 4.34 (s, 2H, CH2N3), 1.80 (bs, 1H, OH); 13C NMR (75 MHz, CDCl3) δ=141.0 (ArCCH2OH), 134.7 (ArCCH2N3), 128.5 (ArCH α to CH2N3), 127.4 (ArCH α to CH2OH), 64.9 (CH2OH), 54.5 (CH2N3).

후처리

  1. additionwas added slowly
  2. customafter which the solvent was evaporated
  3. customThe residue obtained
  4. customwater (50 ml), the phases were separated
  5. washthe organic phase was washed with water (100 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated

출처 및 근거

ORD 기록
ord-0dd7145c94284ab6b2a3b9f72b8f1bff
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09222941B2

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