Ammonium Chloride → HCID 69760958, compound

HRID 1860301Notes

Reaction equation

HRID 1860301 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11]P(OCC)(OCC)=O)=[CH:7][CH:6]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:31][C:32]1([CH3:50])[CH2:40][CH2:39][C:38]([CH3:42])([CH3:41])[C:37]2[CH2:36][C:35]([CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])([CH:43]=O)[CH2:34][C:33]1=2.[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:43]/[C:35]2([CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:34][C:33]3[C:32]([CH3:31])([CH3:50])[CH2:40][CH2:39][C:38]([CH3:42])([CH3:41])[C:37]=3[CH2:36]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 10979490Ethyl 4-((diethoxyphosphoryl)methyl)benzoateHCID 22610231HCID 22610231, compound

Product 1

HCID 69760958HCID 69760958, compoundYield 103.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

0.7 g of 4-(diethoxy-phosphorylmethyl)-benzoic acid ethyl ester were dissolved in 10 ml of THF and treated at −20° C. with 2.2 ml of a 1 molar solution of lithium bis(trimethylsilyl)amide in hexane. After 15 minutes a solution of 0.46 g 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. The reaction mixture was stirred for 3 hours at room temperature, poured on ice cold, saturated aqueous ammonium chloride solution, extracted with ethyl acetate, the organic phase was dried (Na2SO4) and the solvent evaporated. The yellow, oily residue was purified with flash chromatography (silica gel, hexane/10% ethyl acetate) and gave 0.73 g of (E)-4-[2-(4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-yl)-vinyl]-benzoic acid ethyl ester as colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic phase was dried (Na2SO4)
  3. customthe solvent evaporated
  4. customThe yellow, oily residue was purified with flash chromatography (silica gel, hexane/10% ethyl acetate)

Sources & evidence

ORD record
ord-1ce95aab30014f34a45f7dc0818333ce
Source dataset
uspto-grants-2003_03
Patent number
US06528677B1

Reaction notes

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