Water → HCID 516125, compound

HRID 1722766Notes

Reaction equation

HRID 1722766 reaction equation
[CH3:1][C:2]1[CH:19]=[C:18]([C:20]2[N:21]=[N:22][N:23]([CH2:25][C:26](OC)=[O:27])[N:24]=2)[CH:17]=[C:16]([CH3:30])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.CC(O)C.CCCCCC>[CH3:1][C:2]1[CH:19]=[C:18]([C:20]2[N:21]=[N:22][N:23]([CH2:25][CH2:26][OH:27])[N:24]=2)[CH:17]=[C:16]([CH3:30])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 14981840HCID 14981840, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 516125HCID 516125, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21585144Isopropanol hexaneSolvent

Procedure

A solution of 8.0 g 5-{5-[2,6-dimethyl-4- (2-methoxycarbonylmethyl-2H-tetrazol-5-yl)phenoxy]pentyl}-3-methylisoxazole (Example 52) in 50 ml tetrahydrofuran was added dropwise to a stirred suspension of 0.53 g lithium aluminum hydride in 250 ml dry tetrahydrofuran under nitrogen with cooling in an ice bath. The reaction mixture was allowed to come to room temperature and then treated with water and 15% sodium hydroxide. Isolation of the product provided 6.56 g (88%) of 5-{5-[2,6-dimethyl-4-[2-(2-hydroxyethyl)-2H-tetrazol-5-yl]phenoxy]pentyl}-3-methylisoxazole, m.p. 69-70° C. (from 2-propanol/hexane).

Workup

  1. temperaturewith cooling in an ice bath
  2. customto come to room temperature

Sources & evidence

ORD record
ord-ec199993197a4ade90664e2623649308
Source dataset
uspto-grants-1989_08
Patent number
US04857539

Reaction notes

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