Ammonium Chloride → HCID 10069108, compound

HRID 2396626Notes

Reaction equation

HRID 2396626 reaction equation
[Si:1]([O:8][C:9]1[C:17]([CH2:18][CH:19]=[O:20])=[C:16]([O:21][CH3:22])[C:15]([CH3:23])=[C:14]2[C:10]=1[C:11](=[O:24])[O:12][CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:25]([Mg]Br)[CH:26]=[CH2:27].[Cl-].[NH4+]>C1COCC1>[Si:1]([O:8][C:9]1[C:17]([CH2:18][CH:19]([OH:20])[C:26]([CH3:27])=[CH2:25])=[C:16]([O:21][CH3:22])[C:15]([CH3:23])=[C:14]2[C:10]=1[C:11](=[O:24])[O:12][CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10360552HCID 10360552, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 10069108HCID 10069108, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-acetaldehyde (5.25g) in THF (70 ml) at -70° C. was added 1N 2-propenylmagnesium bromide in THF (19 ml). The solution was kept at -40° C. for 15 minutes, then saturated aqueous ammonium chloride (80 ml) was added. The mixture was extracted with ether, and the extract dried and evaporated, to give 4-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-hydroxy-2-methylbut-1-ene, mp 133°-4° C. (tert-butylmethyl ether/hexane).

Workup

  1. extractionThe mixture was extracted with ether
  2. customthe extract dried
  3. customevaporated

Sources & evidence

ORD record
ord-18c2d5891100482687fbbeb4551e8f0d
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

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