Hexane → Ethyl 4-[1-(2,2-dimethoxyethyl)-2-{1(tol-4-yl)3,4-dihydro-4,4-dimethyl-naphthalen-7-yl}-(E)-ethenyl]-benzoate

HRID 1862730Notes

Reaction equation

HRID 1862730 reaction equation
C(OP([C:9]([O:25][CH3:26])([O:23][CH3:24])[CH2:10][CH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=1)(OCC)=O)C.[Li]CCCC.CCCCCC.[C:38]1([CH3:58])[CH:43]=[CH:42][C:41]([C:44]2[C:53]3[C:48](=[CH:49][CH:50]=[C:51]([CH:54]=O)[CH:52]=3)[C:47]([CH3:57])([CH3:56])[CH2:46][CH:45]=2)=[CH:40][CH:39]=1>C1COCC1>[CH3:26][O:25][CH:9]([O:23][CH3:24])[CH2:10]/[C:11](/[C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][CH:22]=1)=[CH:54]\[C:51]1[CH:52]=[C:53]2[C:48]([C:47]([CH3:57])([CH3:56])[CH2:46][CH:45]=[C:44]2[C:41]2[CH:40]=[CH:39][C:38]([CH3:58])=[CH:43][CH:42]=2)=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 57037360Ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoateHCID 865886771-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde2×HCID 178418339Butyllithium

Product 1

HCID 86588679Ethyl 4-[1-(2,2-dimethoxyethyl)-2-{1(tol-4-yl)3,4-dihydro-4,4-dimethyl-naphthalen-7-yl}-(E)-ethenyl]-benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (−78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 350 mg, 0.9 mmol, available in accordance with EPO Application No. 0 210 929 published on Feb. 4, 1987), in THF (9 mL), was added n-BuLi in hexane (1.6M solution, 0.7 mL, 1.1 mmol). The mixture was stirred for 1.5 hours. To this solution 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde (Compound C, 200 mg, 0.72 mmol), in THF (1 mL) was added and the mixture was gradually warmed to ambient temperature (4 h). The reaction was quenched by adding water (5 mL), and extracted with ethyl acetate (3×25 mL). The organic layer was washed with brine (10 mL), dried with MgSO4 and the solvent was removed by distillation. The crude material was purified by silicagel chromatography to afford the title compound as a colorless oil.

Workup

  1. customThe reaction was quenched
  2. additionby adding water (5 mL)
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried with MgSO4
  6. customthe solvent was removed by distillation
  7. customThe crude material was purified by silicagel chromatography

Sources & evidence

ORD record
ord-2288bd62bea446debb5e9035a5cf9c32
Source dataset
uspto-grants-2003_03
Patent number
US06538149B1

Reaction notes

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