Ethyl Acetate → HCID 86653760, compound

HRID 2189060Notes

Reaction equation

HRID 2189060 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].C([O:13][CH2:14][CH3:15])(=O)C>C1COCC1>[C:1]([O:5][C:6](=[O:9])[CH2:7][O:5][C@H:1]1[CH2:3][CH2:15][C@H:14]([OH:13])[CH2:2]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 86653760HCID 86653760, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 2.5 g (24.5 mmol) of cis/trans-cyclopentanediol in 5 ml of THF and, at 0° C., add 16.3 ml (16.3 mmol) of phosphazene base P4-t-Bu (approx. 1M solution in hexane). After 10 min, add the resulting solution dropwise to an ice-cooled solution of 4.77 g (24.5 mmol) of bromoacetic acid tert-butyl ester. After the end of the addition, warm to RT and stir the mixture overnight. Remove fractions of the THF under reduced pressure, dilute with ethyl acetate and wash successively with 1N hydrochloric acid, pH 7 buffer solution and satd. sodium chloride solution, dry over sodium sulphate and concentrate under reduced pressure. From the residue, isolate the product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1→2:1). 631.4 mg (10.7% of theory) of the target compound are obtained as a cis/trans mixture.

Workup

  1. additionAfter the end of the addition
  2. washwash successively with 1N hydrochloric acid, pH 7 buffer solution
  3. dry with materialsodium chloride solution, dry over sodium sulphate
  4. concentrationconcentrate under reduced pressure
  5. customFrom the residue, isolate the product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1→2:1)
  6. custom631.4 mg (10.7% of theory) of the target compound are obtained as a cis/trans mixture

Sources & evidence

ORD record
ord-c928197fe62041d5a3a55276ec1afb8a
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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