1-(Chloromethoxy)-2-methoxyethane → (E)-6-[1,3-Dihydro-6-methoxy-4-[(2-methoxyethoxy)methoxy]-7-methyl-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoic Acid Methyl Ester

HRID 1781522Notes

Reaction equation

HRID 1781522 reaction equation
[OH:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:9]([O:21][CH3:22])[C:8]([CH3:23])=[C:7]2[C:3]=1[C:4](=[O:24])[O:5][CH2:6]2.C(N(C(C)C)CC)(C)C.[CH3:34][O:35][CH2:36][CH2:37][O:38][CH2:39]Cl>C(Cl)Cl>[CH3:22][O:21][C:9]1[C:8]([CH3:23])=[C:7]2[C:3]([C:4](=[O:24])[O:5][CH2:6]2)=[C:2]([O:1][CH2:34][O:35][CH2:36][CH2:37][O:38][CH3:39])[C:10]=1[CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 6478685Methyl (4E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

Product 1

HCID 10342183(E)-6-[1,3-Dihydro-6-methoxy-4-[(2-methoxyethoxy)methoxy]-7-methyl-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (61.0 g) in methylene chloride (1000 ml) at 0° C. was added diisopropylethylamine (30.4 g) and methoxyethoxymethyl chloride (29.2 g). After 31/2 hours the solution was washed with dilute hydrochloric acid, dried and evaporated to give methyl (E)-6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl) -4-methyl-4-hexenoate as an oil.

Workup

  1. washAfter 31/2 hours the solution was washed with dilute hydrochloric acid
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-dfb5a7b7973c4b7fbba91920cc2aedaa
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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