Formaldehyde → HCID 15728720, compound

HRID 1492934Notes

Reaction equation

HRID 1492934 reaction equation
[CH2:1]([SnH:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].C([N-]C(C)C)(C)C.[Li+].[CH2:22]=[O:23].[CH3:24][O:25][CH2:26][CH2:27][O:28][CH2:29]Cl>C1CCCCC1.O1CCCC1>[CH2:10]([Sn:5]([CH2:22][O:23][CH2:29][O:28][CH2:27][CH2:26][O:25][CH3:24])([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 5948TributylstannaneHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 2724682Lithium diisopropylamide

Product 1

HCID 15728720HCID 15728720, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

Tributyltin hydride (2.69 ml, 0.01 mol) was added dropwise to a solution of lithium diisopropylamide (a 1.5M solution in cyclohexane; 6.7 ml, 0.01 mol) in tetrahydrofuran (20 ml) at 0° under argon. After 15 minutes, paraformaldehyde (300 mg, 0.01 mol) was added, followed by 2-methoxyethoxymethyl chloride (1.15 ml, 0.01 mol) after 3 hours. Stirring was continued at room temperature for 12 hours and the mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was flash chromatographed on silica using 5% ethyl ether/petroleum ether. Fractions with Rf of about 0.24 on evaporation afforded the desired ether as a colorless oil (1.11 g, 27%).

Workup

  1. customat 0°
  2. waitwas continued at room temperature for 12 hours
  3. customthe mixture was quenched with water
  4. extractionExtraction (ethyl ether) and evaporation of the
  5. dry with materialdried (magnesium sulphate)
  6. customextracts gave an oil, which
  7. customchromatographed on silica using 5% ethyl ether/petroleum ether
  8. customFractions with Rf of about 0.24 on evaporation
  9. customafforded the desired ether as a colorless oil (1.11 g, 27%)

Sources & evidence

ORD record
ord-4192cea028bf41dc8b07eacef78b6f18
Source dataset
uspto-grants-1994_12
Patent number
US05376676

Reaction notes

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