Sodium Chloride → HCID 89534506, compound

HRID 1528193Notes

Reaction equation

HRID 1528193 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[Mg+2].[Br-].[CH3:12][C:13]1([CH:17]=[O:18])[CH2:16][O:15][CH2:14]1.[Cl-].[Na+]>O1CCCC1>[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH:17]([C:13]2([CH3:12])[CH2:16][O:15][CH2:14]2)[OH:18])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 189624683-Methyloxetane-3-carbaldehydeHCID 66970597HCID 66970597, compound

Product 1

HCID 89534506HCID 89534506, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

1.0 M Magnesium m-methoxybenzene bromide in tetrahydrofuran (25 ml, 25.0 mmol) was added dropwise to a solution of 3-methyloxetane-3-carbaldehyde (0.5 g, 5.0 mmol) in 8 ml of tetrahydrofuran cooled to −70° C. The reaction medium was stirred for 4 hours at −70° C. and then allowed to return to 0° C., hydrolyzed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, washed with a saturated sodium chloride solution and evaporated. The residue obtained was purified by chromatography on a cartridge of silica gel (eluted with heptane/ethyl acetate, gradient from 90/10 to 60/40). 0.45 g of product was obtained in the form of a thick colorless oil. Yield=43%.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with a saturated sodium chloride solution
  3. customevaporated
  4. customThe residue obtained
  5. customwas purified by chromatography on a cartridge of silica gel (eluted with heptane/ethyl acetate, gradient from 90/10 to 60/40)

Sources & evidence

ORD record
ord-07e8d1e2d6f440dcbfea06ee57643bd0
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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