Tetrahydrofuran → HCID 19991618, compound

HRID 345899Notes

Reaction equation

HRID 345899 reaction equation
C([Li])CCC.[CH:6]#[C:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]CCC.[CH2:19]([Si:21]([CH2:33][CH3:34])([CH2:31][CH3:32])[C:22]1[O:23][CH:24]=[C:25]([CH:27]([CH3:30])C=O)[CH:26]=1)[CH3:20].[O:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>>[OH:35][CH:36]([C:37]#[C:38][CH2:39][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:30][CH2:27][C:25]1[CH:26]=[C:22]([Si:21]([CH2:19][CH3:20])([CH2:31][CH3:32])[CH2:33][CH3:34])[O:23][CH:24]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 1177541-TridecyneHCID 88522844HCID 88522844, compoundHCID 178418339Butyllithium

Product 1

HCID 19991618HCID 19991618, compound

Procedure

n-Butyl lithium (a 2.5M solution in tetrahydrofuran; 0.58 ml, 1.44 mmol) was added dropwise to a solution of 1-tridecyne (259 mg, 1.44 mmol) in tetrahydrofuran (6 ml) at 0°. After 1 hour, a solution of (2-triethylsilyl-4-furyl)-1-propanal (312 mg, 1.31 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by a silica column using 15% ethyl ether/hexane to give the titled alcohol.

Workup

  1. waitwas continued for 14 hours, while the cooling bath attained room temperature
  2. customThe mixture was quenched with water
  3. extractionwas extracted with ethyl ether
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave an oil, which
  7. customwas purified by a silica column

Sources & evidence

ORD record
ord-0610830811c640daaa91fc4785d2a236
Source dataset
uspto-grants-1991_10
Patent number
US05059611

Reaction notes

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