Formaldehyde → 67727-01-9

HRID 2254914Notes

Reaction equation

HRID 2254914 reaction equation
[O:1]([CH2:8][C:9]#[CH:10])[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][O:3]1.[Li]CCCC.C=O.[C:18](Cl)(Cl)(Cl)[Cl:19]>C1COCC1>[O:1]([CH2:8][C:9]#[C:10][CH2:18][Cl:19])[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][O:3]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5943Carbon TetrachlorideHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 178418339Butyllithium

Product 1

HCID 55891167727-01-9Yield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

THPO-CH2C≡CH was treated with 1.1 equivalents of n-BuLi in THF at -78° C. for 0.5 hours and then 1.4 equivalents of paraformaldehyde ((CH2O)n) Over the course of 12 hours, the reaction was allowed to rise to 25° C. and a product isolated in 84% yield. This product was then treated with 1.6 equivalents of P(oct)3 in CCl4 at 25° C. for six hours, yielding THPO-CH2C≡CCH2Cl in 85% yield. This compound was then treated with 1.0 equivalents NA2S.9H2O in EtOH:H2O (10:1) at 25° C. for 12 hours. The product, which was isolated in 47% yield, was then treated with acetic acid (AcOH):H2O:THF (7:3:10) at 25° C. for 12 hours. The resulting product, which was isolated in 64% yield, was then treated with 3.0 equivalents of mCPBA in methylene chloride for 2 hours yielding a compound having structure (2) (R3 =R5 =H, R2 =R4 =CH2OH) in 40% yield.

Workup

  1. customOver the course of 12 hours
  2. customto rise to 25° C.
  3. customa product isolated in 84% yield

Sources & evidence

ORD record
ord-a5a8ecc313704a25aa6361f9e829263c
Source dataset
uspto-grants-1993_08
Patent number
US05237101

Reaction notes

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