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

HRID 1509360ノート

反応式

HRID 1509360 の反応式
[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]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 574448534-(Azidomethyl)benzaldehyde

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0dd7145c94284ab6b2a3b9f72b8f1bff
出典データセット
uspto-grants-2015_12
特許番号
US09222941B2

反応ノート

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