Water → HCID 86761083, compound

HRID 644570Notes

Reaction equation

HRID 644570 reaction equation
[H-].[Na+].[Si:3]([O:10][CH2:11][CH2:12][CH:13]=O)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[OH2:15].[CH2:16]1[CH2:20][O:19][CH2:18][CH2:17]1>>[Si:3]([O:10][C:11]1[CH:12]=[C:13](/[C:11](/[CH2:12][CH3:13])=[CH:17]/[C:18]([O:19][CH2:20][CH3:16])=[O:15])[CH:7]=[CH:6][CH:8]=1)([C:6]([CH3:7])([CH3:8])[CH3:9])([CH3:4])[CH3:5]

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 36623923-((Tert-butyldimethylsilyl)oxy)propanal

Product 1

HCID 86761083HCID 86761083, compound

Procedure

22.5 ml (113 mmol) of triethyl phosphono-acetate are dissolved in 100 ml of THF. 4.5 g (113 mmol) of 60% sodium hydride are then added, and the medium is stirred for 30 minutes at ambient temperature. A solution of 20 g (75.6 mmol) of 3-(tert-butyldimethylsilanyloxy)propan-1-one in 100 ml of THF is then added drop by drop. The medium is stirred for 6 hours, then treated with water and extracted with ethyl acetate. The residue obtained is purified by chromatography on silica gel (eluent ethyl acetate 10-heptane 90). A yellow oil is obtained (m=7.6 g; Y=30%).

Workup

  1. stirringThe medium is stirred for 6 hours
  2. extractionextracted with ethyl acetate
  3. customThe residue obtained
  4. customis purified by chromatography on silica gel (eluent ethyl acetate 10-heptane 90)
  5. customA yellow oil is obtained (m=7.6 g; Y=30%)

Sources & evidence

ORD record
ord-4a12295d5f6f46fbb07a021e74e9ac5c
Source dataset
uspto-grants-2010_04
Patent number
US07700657B2

Reaction notes

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