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Methyl bromoacetate → HCID 10714451, compound

HRID 322869
Notes
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Reaction equation

HRID 322869 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:16])[CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 10542398HCID 10542398, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10714451HCID 10714451, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

A stirred solution of benzyl 3-benzyloxyphenyl ketone (3.02 g) in dry tetrahydrofuran (70 mL) at −40° C. is treated with potassium tert-butoxide (1.12 g), portionwise during 10 minutes. The reaction is stirred at −40° C. for 1 hour and is then treated dropwise with a solution of methyl bromoacetate (1.04 g) in tetrahydrofuran (10 mL). The mixture is allowed to stir at ambient temperature for 18 hours. After this time, the reaction is concentrated to dryness and partitioned between ethyl acetate and water. The organic layer is dried over magnesium sulphate and concentrated under reduced pressure. The residue is recrystallised from a mixture of ethyl acetate and pentane, to give methyl (RS)-4-(3-benzyloxyphenyl)-4-oxo-3-phenylbutanoate (1.4 g), m.p. 88-89° C.

Workup

  1. stirringto stir at ambient temperature for 18 hours
  2. concentrationAfter this time, the reaction is concentrated to dryness
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer is dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is recrystallised from a mixture of ethyl acetate and pentane

Sources & evidence

ORD record
ord-70563135398d4a2db094d39ddc19f5bf
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211234B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes