Sodium Methoxide → HCID 53880467, compound

HRID 1602696Notes

Reaction equation

HRID 1602696 reaction equation
C[O-].[Na+].[CH3:4][C:5]1([CH3:32])[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]2[CH:10]=[C:9]([C:17]([CH2:19][O:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=3[I:31])=O)[CH:8]=[CH:7][C:6]1=2.[Br-].[CH3:34]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[I:31][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][C:21]=1[O:20][CH:19]=[C:17]([C:9]1[CH:8]=[CH:7][C:6]2[C:5]([CH3:4])([CH3:32])[CH2:14][CH2:13][C:12]([CH3:15])([CH3:16])[C:11]=2[CH:10]=1)[CH3:34])[C:25]([O:27][CH3:28])=[O:26]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 19353141HCID 19353141, compoundHCID 178503020HCID 178503020, compound

Product 1

HCID 53880467HCID 53880467, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30% sodium methoxide solution (2.67 g, 14.83 mmol) is added over 8 hours to a mixture of methyl 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl)methoxy]-3-iodobenzoate (7.50 g, 14.8 mmol) and methyltriphenylphosphine bromide (7.30 g, 20.42 mmol) in THF (80 ml). The mixture is stirred for 18 hours at room temperature. The mixture is concentrated on a rotary evaporator under vacuum at 40° C. This is extracted with 90 ml of ethyl ether and 90 ml of water. After separation of the phases by settling, the organic phase is washed twice with 90 ml of water, dried over anhydrous magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The product is purified by flash chromatography on a column of silica (70% CH2Cl2, 30% heptane).

Workup

  1. concentrationThe mixture is concentrated on a rotary evaporator under vacuum at 40° C
  2. extractionThis is extracted with 90 ml of ethyl ether and 90 ml of water
  3. customAfter separation of the phases
  4. washthe organic phase is washed twice with 90 ml of water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  7. customThe product is purified by flash chromatography on a column of silica (70% CH2Cl2, 30% heptane)

Sources & evidence

ORD record
ord-d3a528bffd4f453fb7edb7a1959d52e9
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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