Tetrahydrofuran → HCID 15218718, compound

HRID 376015Notes

Reaction equation

HRID 376015 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].[Li]N([Si](C)(C)C)[Si](C)(C)C.[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1.[Cl-].[NH4+].[CH2:24]1[CH2:28]OC[CH2:25]1>>[CH:17]1([CH:21]([OH:20])[C:3]#[C:2][C:1]([O:5][CH3:6])=[O:4])[CH2:18][CH2:19][CH2:28][CH2:24][CH2:25]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 13536Methyl propiolate2×HCID 25517Ammonium ChlorideHCID 178420700HCID 178420700, compound

Product 1

HCID 15218718HCID 15218718, compound

Procedure

Under nitrogen flow, a solution of methyl propiolate (compound 6) (1.68 g; 20.0 mmoles) in 4 ml of dry THF was added dropwise to a solution of 20.0 ml (20.0 mmoles) of 1M LiN(TMS)2 -THF in 40 ml of dry THF at -78° C. After completion of the addition, the reaction solution was stirred for 1 hour, and a solution of 2.24 g (20.0 mmoles) of cyclohexanecarboxyaldehyde (compound 9k) in 5 ml of dry THF was added dropwise thereto. The mixture was stirred for additional 1 hour, a saturated aqueous ammonium chloride was added to the reaction solution and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a crude product of the desired alcohol 10k as an oil. This was used in the next reaction without further purification.

Workup

  1. additionAfter completion of the addition
  2. stirringThe mixture was stirred for additional 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff69f83474834e0c8f88881350c6a128
Source dataset
uspto-grants-1996_01
Patent number
US05488134

Reaction notes

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