Diethyl Ether → HCID 59526205, compound

HRID 385699Notes

Reaction equation

HRID 385699 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][C:7](C(OC)=O)=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[CH3:14][Mg]Br.C([O:19][CH2:20][CH3:21])C.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C:4]1[CH:13]=[CH:12][C:7]([C:20]([OH:19])([CH3:21])[CH3:14])=[CH:6][CH:5]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 11116577HCID 11116577, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59526205HCID 59526205, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-allylbenzoate (5.66 g, 32.1 mmol) in tetrahydrofuran (37 mL) at 0° C. under an argon atmosphere was charged with a solution of methyl magnesium bromide in diethyl ether (3 M, 26.8 mL, 80 mmol). The reaction mixture was allowed to warm to room temperature and then it was cooled to 0° C. after an additional four hours, at which time a saturated aqueous ammonium chloride solution (50 mL) was added slowly followed by diethyl ether (100 mL). The layers were separated, and the aqueous layer was extracted with diethyl ether (2×50 mL) The combined organic layers were dried over magnesium sulfate, filtered, and concentrated to afford the title compound.

Workup

  1. additionwas added slowly
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with diethyl ether (2×50 mL) The combined organic layers
  4. dry with materialwere dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7461c689a701493aacedde2d322c27bf
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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