Sodium Hydroxide → HCID 53924634, compound

HRID 463660Notes

Reaction equation

HRID 463660 reaction equation
[OH-].[Na+].[CH2:3]([O:10][CH2:11][C:12]1[N:16]([CH2:17][C:18]([O:20]CC)=[O:19])[N:15]=[N:14][N:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C.O1CCCC1>[CH2:3]([O:10][CH2:11][C:12]1[N:16]([CH2:17][C:18]([OH:20])=[O:19])[N:15]=[N:14][N:13]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54049519HCID 54049519, compound

Product 1

HCID 53924634HCID 53924634, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 2.5N sodium hydroxide solution (100 ml, 0.25 mol) was added dropwise over fifteen minutes to ethyl 5-(1-benzyloxymethyl)tetrazolyl acetate 2 (36.21 gm, 0.131 mol) in 800 ml ethanol and 200 ml tetrahydrofuran at room temperature, causing a white precipitate. After one hour, the mixture was concentrated in vacuo. On liter of water was added and the aqueous phase was washed with two 400 ml portions of dichloromethane. The aqueous phase was acidified with 150 ml 2.5N hydrochloric acid and extracted with three 500 ml portions of ethyl acetate. The combined ethyl acetate extracts were dried over magnesium sulfate. Concentration in vacuo and trituration of the white solid from diethyl ether yielded 27.24 gm (84%) 5-(1-benzyloxymethyl)tetrazolylacetic acid 3 as a white solid: mp 125°-126°; 1H NMR (CDCl3 :DMSO d6, 10:1) δ 7.40 (5H, m), 5.87 (2H, S), 4.55 (2H, S), 4.09 (2H, S) mass spectrum FD 249 (M+H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionOn liter of water was added
  3. washthe aqueous phase was washed with two 400 ml portions of dichloromethane
  4. extractionextracted with three 500 ml portions of ethyl acetate
  5. dry with materialThe combined ethyl acetate extracts were dried over magnesium sulfate
  6. concentrationConcentration in vacuo and trituration of the white solid from diethyl ether

Sources & evidence

ORD record
ord-ca0d0238e59f4b749f46d2e42f05d3d3
Source dataset
uspto-grants-1985_10
Patent number
US04544557

Reaction notes

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