Ethyl Acetate → methyl (Z)-3-{3-[5-(tert-butyldimethylsilyloxy)-pentyloxy]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl}-2-butenoate

HRID 1415909Notes

Reaction equation

HRID 1415909 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:16](B(O)O)=[CH:17][C:18]2[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=2[CH:24]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.I/[C:45](/[CH3:51])=[CH:46]\[C:47]([O:49][CH3:50])=[O:48]>O.C(COC)OC>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:16](/[C:45](/[CH3:51])=[CH:46]\[C:47]([O:49][CH3:50])=[O:48])=[CH:17][C:18]2[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=2[CH:24]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10900307HCID 10900307, compound2×HCID 86754091HCID 86754091, compound

Product 1

HCID 86754090methyl (Z)-3-{3-[5-(tert-butyldimethylsilyloxy)-pentyloxy]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl}-2-butenoate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of tetrakis(triphenyl-phosphine)palladium (155 mg), 3-[5-(tert-butyldimethylsilyloxy)pentyloxy]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaleneboronic acid (300 mg, 0.67 mmol), a 2M solution of potassium carbonate in water (0.67 ml) and methyl (Z)-3-iodo-2-butenoate (Ma, S. & Lu, X.; J. Chem. Soc. Chem. Com., pp. 1643-1644 (1990)) (182 mg) in dimethoxyethane (DME) (10 ml) was heated to reflux for 24 h. The solution was poured into a mixture of water and ethyl acetate. The organic phase was washed twice with water, dried over magnesium sulfate and concentrated in a rotary evaporator under vacuum at 40° C. The desired compound was purified by flash chromatography on a silica column.

Workup

  1. temperatureto reflux for 24 h
  2. washThe organic phase was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in a rotary evaporator under vacuum at 40° C
  5. customThe desired compound was purified by flash chromatography on a silica column

Sources & evidence

ORD record
ord-bb5b252a16af4043b7f0f2fda92da538
Source dataset
uspto-grants-1999_06
Patent number
US05910508

Reaction notes

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