Ammonium Chloride → HCID 20348360, compound

HRID 1704280Notes

Reaction equation

HRID 1704280 reaction equation
[C:1]([C:4]1([O:13][CH3:14])[C:8]([O:9][CH3:10])=[CH:7][CH:6]([O:11][CH3:12])[O:5]1)(=[O:3])[CH3:2].[BH4-].[Na+].[NH4+].[Cl-]>CO>[OH:3][CH:1]([C:4]1([O:13][CH3:14])[C:8]([O:9][CH3:10])=[CH:7][CH:6]([O:11][CH3:12])[O:5]1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 20348362HCID 20348362, compound

Product 1

HCID 20348360HCID 20348360, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2-acetyl-2,3,5-trimethoxy-2,5-dihydrofuran (9.22 g, 0.049 moles) was dissolved in 100 ml of methanol and cooled to 0° C. Solid NaBH4 (4.0 g, 0.105 moles) was added portion-wise over 1 hour, maintaining a temperature below 15° C. The reaction was then allowed to warm to room temperature, and 20 ml of saturated aqueous NH4Cl added. Extraction of the crude product with chloroform and concentration yielded 9.3 g of 2-(1-hydroxyethyl)-2,3,5-trimethoxy-2,5-dihydrofuran (100%) as a clear 0.1, NMR (CDCl3 + D2O, δ) 5.5 (1H, m), 5.03 (1H, M), 3.8 (4H, m), 3.58 (3H, s), 3.3 (3H, s), 1.10 (3H, t).

Workup

  1. temperaturemaintaining a temperature below 15° C
  2. temperatureto warm to room temperature
  3. extractionExtraction of the crude product
  4. concentrationwith chloroform and concentration

Sources & evidence

ORD record
ord-4b13cbe85ed042a288d95a2947a4b56d
Source dataset
uspto-grants-1978_11
Patent number
US04126624

Reaction notes

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