Chlorotrimethylsilane → Ethyl 4-hydroxy-6-methyl-2-heptynoate

HRID 1835156Notes

Reaction equation

HRID 1835156 reaction equation
C([Li])CCC.[C:6]([O:10][CH2:11][CH3:12])(=[O:9])[C:7]#[CH:8].[CH:13](=[O:18])[CH2:14][CH:15]([CH3:17])[CH3:16].C[Si](Cl)(C)C>O1CCCC1.O>[OH:18][CH:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:8]#[C:7][C:6]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 115523-MethylbutanalHCID 12182Ethyl propiolateHCID 178418339Butyllithium

Product 1

HCID 23503233Ethyl 4-hydroxy-6-methyl-2-heptynoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyl lithium (2.5M in hexanes, 22.5 ml) was added dropwise over 40 minutes with stirring to fresh ethyl propiolate (6.0 ml) in dry tetrahydrofuran (75 ml) under nitrogen, with the temperature being maintained below −68° by external cooling. After 30 minutes, isovaleraldehyde (6.5 ml) in dry tetrahydrofuran (15 ml) was added over 15 minutes with the temperature maintained below −69°. After one hour, trimethylsilyl chloride (10 ml) was added and the reaction was allowed to warm to room temperature. Water was added and the mixture was extracted with ethyl acetate, which was washed with brine, dried, and evaporated to give ethyl 4hydroxy-6-methyl-2-heptynoate as an oil (9.5 g).

Workup

  1. temperaturebeing maintained below −68° by external cooling
  2. temperaturemaintained below −69°
  3. waitAfter one hour
  4. extractionthe mixture was extracted with ethyl acetate, which
  5. washwas washed with brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-59196a5683f4409584345413c022f1c9
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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