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

HRID 1989888Notes

Reaction equation

HRID 1989888 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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.

Sources & evidence

ORD record
ord-7a7a1426d126424f9b2dc37f16b00132
Source dataset
uspto-grants-2010_01
Patent number
US07642263B2

Reaction notes

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