Hydrochloric Acid → HCID 86589630, compound

HRID 1860305Notes

Reaction equation

HRID 1860305 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[C:6]([CH3:18])[CH:7]=[CH:8][CH2:9]P(OCC)(OCC)=O)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:30][C:31]1([CH3:49])[CH2:39][CH2:38][C:37]([CH3:41])([CH3:40])[C:36]2[CH2:35][C:34]([CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])([CH:42]=O)[CH2:33][C:32]1=2.Cl>C1COCC1.CCCCCC>[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[C:6]([CH3:18])[CH:7]=[CH:8][CH:9]=[CH:42][C:34]1([CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:33][C:32]2[C:31]([CH3:30])([CH3:49])[CH2:39][CH2:38][C:37]([CH3:41])([CH3:40])[C:36]=2[CH2:35]1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 22610231HCID 22610231, compoundHCID 54401923HCID 54401923, compound

Product 1

HCID 86589630HCID 86589630, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

680 mg of 6-(diethoxyphosphoryl)-3-methyl-hexa-2,4-dienoic acid ethyl ester were dissolved in 10 ml of THF and treated dropwise with 2.25 ml of a 1 molar solution of lithium bis(trimethylsilyl)amide in hexane at −78° C. After 10 minutes of stirring, a solution of 500 mg of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carbaldehyde in 5 ml of THF was added dropwise at −78° C. The reaction mixture was slowly warmed to −40° C. and kept at this temperature for 3 hours. The cold reaction mixture was poured in ice/water, acidified with 1 N HCl and extracted with ether. The organic phase was washed with water, dried (Na2SO4) and the solvent was evaporated. The crude oil was purified with medium pressure chromatography (silica gel, hexane/tert.-butyl methyl ether 1%) to give 250 mg of pure (2Z, 4E, 6E)-3-methyl-7-(4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-inden-2-yl)-hepta-2,4,6-trienoic acid ethyl ester and 400 mg of (2E, 4E, 6E)-3-methyl-7-(4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-inden-2-yl)-hepta-2,4,6-trienoic acid ethyl ester as colorless oils.

Workup

  1. waitkept at this temperature for 3 hours
  2. customThe cold reaction mixture
  3. extractionextracted with ether
  4. washThe organic phase was washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was evaporated
  7. customThe crude oil was purified with medium pressure chromatography (silica gel, hexane/tert.-butyl methyl ether 1%)

Sources & evidence

ORD record
ord-8f39717ad4684afea278a8d46a57770e
Source dataset
uspto-grants-2003_03
Patent number
US06528677B1

Reaction notes

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