Imidazole → (2R)-1-{[Tri(propan-2-yl)silyl]oxy}propan-2-ol

HRID 1011672

反応式

HRID 1011672 の反応式
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[CH2:12]([OH:16])[C@H:13]([OH:15])[CH3:14].N1C=CN=C1>CN(C=O)C>[CH:1]([Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[O:16][CH2:12][C@H:13]([OH:15])[CH3:14])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 259994R-(-)-1,2-Propanediol

生成物 1

HCID 57504697(2R)-1-{[Tri(propan-2-yl)silyl]oxy}propan-2-ol収率 76.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Triisopropylsilyl chloride (83.8 mL, 390 mmol) was added slowly over 15 minutes to a solution of (2R)-propane-1,2-diol (29.7 g, 390 mmol) in DMF at 0° C. (100 mL) keeping the internal temperature below 15° C. This was followed by addition of imidazole (66.4 g, 975 mmol) and the reaction mixture was allowed to warm to RT and stirred under argon for 20 hours. The reaction was quenched with 1M hydrochloric acid/diethyl ether (300 mL/800 mL). The organic layer was separated and washed with 1M hydrochloric acid followed by saturated brine solution. The organic layer was dried (MgSO4), filtered and evaporated. Purification by distillation at 10 mmHg, 90-104° C., afforded the title compound as colourless oil (69.5 g). 1H NMR δ (CDCl3): 1.05 (s, 18H), 1.05-1.1 (m, 3H), 1.05 (d, 3H), 2.55 (s, 1H), 3.45 (dd, 1H), 3.7 (dd, 1H), 3.85 (m, 1H).

後処理

  1. customthe internal temperature below 15° C
  2. customThe reaction was quenched with 1M hydrochloric acid/diethyl ether (300 mL/800 mL)
  3. customThe organic layer was separated
  4. washwashed with 1M hydrochloric acid
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification
  9. distillationby distillation at 10 mmHg, 90-104° C.

出典と根拠

ORDレコード
ord-86d510f0f03347fd8ec15a5176c3ecb7
出典データセット
uspto-grants-2011_07
特許番号
US07977328B2

関連ノート

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