Solketal → HCID 90135527, compound

HRID 1483040Notes

Reaction equation

HRID 1483040 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[Na].Br[CH2:12][C:13]([CH:15]1[CH2:17][CH2:16]1)=[O:14]>>[CH:15]1([C:13](=[O:14])[CH2:12][O:8][CH2:7][CH:5]2[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]2)[CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 7528SolketalHCID 5360545SodiumHCID 109208412-Bromo-1-cyclopropylethan-1-one

Product 1

HCID 90135527HCID 90135527, compound

Conditions

Temperature
85 °C

Procedure

Charge a flask with (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (10 g, 75.7 mmol), heat to 85° C. and add freshly cut sodium (465 mg, 20.23 mmol) Heat to 85° C. and stir for 1 hour. Add 2-bromo-1-cyclopropylethanone (3.0 g, 18.4 mmol) maintain the temperature at 85° C. and stir for 30 minutes. Filter and wash the solid with ACN (20 mL). Collect the filtrate and concentrate under reduced pressure. Purify via HPLC conditions Z to give the title compound as a colorless oil. (650 mg, 16.5%). MS (m/z): 215 (M+1).

Workup

  1. temperatureHeat to 85° C.
  2. stirringstir for 30 minutes
  3. filtrationFilter
  4. washwash the solid with ACN (20 mL)
  5. customCollect the filtrate
  6. concentrationconcentrate under reduced pressure
  7. customPurify via HPLC conditions Z

Sources & evidence

ORD record
ord-c41ba0d2504944a088f4b50a19ea9cb8
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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