Water → HCID 57835837, compound

HRID 731169Notes

Reaction equation

HRID 731169 reaction equation
[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][C:12]([CH2:13][C:14]2[O:15][C:16]([CH3:19])=[CH:17][N:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][C:12]([CH:13]([C:14]2[O:15][C:16]([CH3:19])=[CH:17][N:18]=2)[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 57835885HCID 57835885, compound

Product 1

HCID 57835837HCID 57835837, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(benzyloxy)benzyl)-5-methyloxazole (M5.2) (3.23 mmol) in THF (25 mL) at −78° C., was added dropwise LDA (4.5 mmol). The mixture was stirred for 18 minutes, followed by addition of ethyl bromoacetate (4.5 mmol). It was allowed to warm to room temperature for 3 hours, followed by addition of water, which was extracted with EtOAc. The extract was washed with brine and dried over Na2SO4 using standard work up conditions. Column chromatography (⅓ EtOAc/hexane) of the residue afforded compound M5.3. MS ESI (pos.) m/e: 366 (M+H).

Workup

  1. extractionwas extracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4 using standard work up conditions

Sources & evidence

ORD record
ord-1cdc4591f0c24302a500cd4aa293d00f
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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