Sodium hydride → (2R)-2-(oxetan-3-yloxy)-2-phenylethan-1-ol

HRID 870485Notes

Reaction equation

HRID 870485 reaction equation
[C:1]1([C@H:7]2[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:10]1[CH2:13][CH:12]([OH:14])[CH2:11]1.[H-].[Na+]>>[O:10]1[CH2:13][CH:12]([O:14][C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][OH:8])[CH2:11]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 114946(S)-styrene oxideHCID 9942117Oxetan-3-ol

Product 1

HCID 86684708(2R)-2-(oxetan-3-yloxy)-2-phenylethan-1-olYield 25%

Conditions

Temperature
80 °C

Procedure

Into a 50-mL round-bottom flask was placed (2S)-2-phenyloxirane (4 g, 33.29 mmol, 1.00 equiv) and oxetan-3-ol (16 mL). This was followed by the addition of sodium hydride (1.3 g, 32.50 mmol, 1.00 equiv, 60%) in several batches. The resulting solution was stirred for 1 h at 80° C. in an oil bath. The reaction was then quenched by the addition of 50 mL of NH4Cl (sat., aq.). The resulting solution was extracted with 2×50 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with PE/EA (8:1). Purification afforded 1.6 g (25%) of (2R)-2-(oxetan-3-yloxy)-2-phenylethan-1-ol (73.2) as a yellow oil.

Workup

  1. customInto a 50-mL round-bottom flask was placed
  2. customThe reaction was then quenched by the addition of 50 mL of NH4Cl (sat., aq.)
  3. extractionThe resulting solution was extracted with 2×50 mL of ethyl acetate
  4. concentrationconcentrated under vacuum
  5. customPurification

Sources & evidence

ORD record
ord-986e96d025cc48f080ab447bdbebafd1
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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