Water → 2-(6-(1H-tetrazol-1-yl)pyridin-3-yl)ethanol

HRID 1519534Notes

Reaction equation

HRID 1519534 reaction equation
[Li+].[BH4-].C([O:5][C:6](=O)[CH2:7][C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH:18]=[N:17][N:16]=[N:15]2)=[CH:12][CH:13]=1)C.O>C1COCC1>[N:14]1([C:11]2[N:10]=[CH:9][C:8]([CH2:7][CH2:6][OH:5])=[CH:13][CH:12]=2)[CH:18]=[N:17][N:16]=[N:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 77230693ethyl [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate

Product 1

HCID 675168232-(6-(1H-tetrazol-1-yl)pyridin-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiBH4 (0.48 mL, 0.96 mmol, 2 M in THF) was added to a stirred solution of ethyl[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate (0.150 g, 0.64 mmol) in THF (20 ml) at 0° C. The resulting solution was stirred for 12 h. Water (5 ml) was added, and the resulting solution was extracted with dichloromethane (2×50 ml). The combined organic layers were dried over MgSO4, filtered, and evaporated under reduced pressure to yield the product after flash chromatography (eluted with 10-50% ethyl acetate in hexanes) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 9.51 (s, 1H), 8.43 (br s, 1H), 8.01 (dd, J=2.7, J=2.7 Hz, 1H), 7.91 (dd, J=2.1, J=2.0 Hz, 1H), 3.99 (br s, 2H), 3.00 (t, J=6.1, J=6.2 Hz, 2H). LC-MS (IE, m/z): 164.1 [(M+1)+−28].

Workup

  1. extractionthe resulting solution was extracted with dichloromethane (2×50 ml)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto yield the product
  6. washafter flash chromatography (eluted with 10-50% ethyl acetate in hexanes) as a colorless oil

Sources & evidence

ORD record
ord-bc66a0a0d32d4c4ea4ce1220ca9e21e4
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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