Bromoacetic Acid → HCID 67216757, compound

HRID 468595Notes

Reaction equation

HRID 468595 reaction equation
[H-].[Na+].Br[CH2:4][C:5]([OH:7])=[O:6].CN(C=O)C.[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][CH2:20][CH2:21][OH:22]>C1COCC1>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][CH2:20][CH2:21][O:22][CH2:4][C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 6227Bromoacetic AcidHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 41668332-(Oxan-2-yloxy)ethan-1-ol

Product 1

HCID 67216757HCID 67216757, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of NaH (60% dispersion in mineral oil, 4.80 g, 120 mmol) in THF, at 0° C., was added a THF solution (15 ml) of bromoacetic acid (6.11 g, 44 mmol). Mixture was stirred at room temperature 0.5 hr, then a DMF solution (15 ml) of alcohol 1 (5.84 g, 40 mmol) was added dropwise. Mixture was stirred at room temperature for 17 hrs then quenched with H2O and extracted twice with ether. Aqueous layer was acidified to pH 2-3 and extracted with EtOAc. Combined organic layers were dried over MgSO4, filtered and concentrated to give pure compound 2 as a pale yellow oil (6.93 g, 85%) used for next step without further purification.

Workup

  1. stirringMixture was stirred at room temperature for 17 hrs
  2. customthen quenched with H2O
  3. extractionextracted twice with ether
  4. extractionextracted with EtOAc
  5. dry with materialCombined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6e10519278a14ee691c1b078d2e893ae
Source dataset
uspto-grants-2014_01
Patent number
US08624044B2

Reaction notes

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