Hydrochloric Acid → HCID 19353145, compound

HRID 378222Notes

Reaction equation

HRID 378222 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[SH:14])[C:7]([O:9][CH3:10])=[O:8].Br[CH2:16][C:17]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]2([CH3:32])[CH3:31])=[CH2:18].Cl>CN(C=O)C.C(OCC)C>[I:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[S:14][CH2:18][C:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=2[CH:20]=1)=[CH2:16])[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 19353153HCID 19353153, compoundHCID 19353170HCID 19353170, compound

Product 1

HCID 19353145HCID 19353145, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

75% NaH (115 mg, 3.58 mmol) is added to a solution of methyl 3-Iodo-4-mercaptobenzoate (531 mg, 3.25 mmol) in DMF (20 ml) at 0° C. Stirring is continued for 20 min at ambient temperature, then a solution of 6-(1-bromomethylvinyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (1 g, 3.25 mmol) in DMF (5 ml) is added dropwise. The mixture is stirred for 2 h at ambient temperature, and treated with an aqueous hydrochloric acid solution and ethyl ether. The organic phase is washed twice with water, dried over magnesium sulphate, and concentrated in vacuo at 40° C. in a rotary evaporator. The product is purified by flash chromatography on a silica column (CH2Cl2 50% heptane 50%).

Workup

  1. stirringThe mixture is stirred for 2 h at ambient temperature
  2. washThe organic phase is washed twice with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo at 40° C. in a rotary evaporator
  5. customThe product is purified by flash chromatography on a silica column (CH2Cl2 50% heptane 50%)

Sources & evidence

ORD record
ord-fc64c1ea3d16459e9b2bd2da180995cd
Source dataset
uspto-grants-2000_02
Patent number
US06030952

Reaction notes

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