Sodium Hydroxide → 2-(4-Bromophenyl)-5,8-dioxaspiro[3.4]octane-2-carboxylic acid

HRID 221972Notes

Reaction equation

HRID 221972 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:14][C:15]2([CH2:20]Cl)[O:19][CH2:18][CH2:17][O:16]2)[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].[OH-].[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:9]([OH:11])=[O:10])[CH2:14][C:15]3([O:16][CH2:17][CH2:18][O:19]3)[CH2:20]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 59161535Ethyl 2-(4-bromophenyl)-3-(2-(chloromethyl)-1,3-dioxolan-2-yl)propanoate

Product 1

HCID 591615152-(4-Bromophenyl)-5,8-dioxaspiro[3.4]octane-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 2-(4-bromophenyl)-3-[2-(chloromethyl)-1,3-dioxolan-2-yl]propanoate (1-3) (27 g, 71.5 mmol) cooled to −78° C. in DMF (200 mL) was added NaH (8.58 g, 214 mmol) and the reaction was allowed to slowly warm from −78° C. to rt. Once at rt, 1N NaOH (100 mL) was added and the reaction mixture was stirred over night. The crude reaction mixture was poured into saturated sodium bicarbonate and washed with chloroform. The aqueous layer was acidified with HCl, extracted with chloroform, dried over sodium sulfate filtered and concentrated. The crude residue was purified by column chromatography eluting with 1-50% EtOAc/Hexane. The appropriate fractions were concentrated and recrystallized from EtOAc/hexane to give 2-(4-bromophenyl)-5,8-dioxaspiro[3.4]octane-2-carboxylic acid (1-4) as a white solid. MS (M+H)+: 314.

Workup

  1. temperatureto slowly warm from −78° C. to rt
  2. customThe crude reaction mixture
  3. washwashed with chloroform
  4. extractionextracted with chloroform
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by column chromatography
  9. washeluting with 1-50% EtOAc/Hexane
  10. concentrationThe appropriate fractions were concentrated
  11. customrecrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-90ec1c63679341569c7e0360a3c59bf1
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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