Chloromethyl Methyl Ether → 1-(3-Methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one

HRID 1883275Notes

Reaction equation

HRID 1883275 reaction equation
[OH:1][C:2]1[C:3]([C:16](=[O:19])[CH2:17][CH3:18])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.Cl[CH2:21][O:22][CH3:23]>CCN(C(C)C)C(C)C>[CH3:21][O:22][CH2:23][O:1][C:2]1[C:3]([C:16](=[O:19])[CH2:17][CH3:18])=[CH:4][C:5]2[C:6]([CH3:14])([CH3:15])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 235108275,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl ethyl ketone2×

Product 1

HCID 235108151-(3-Methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-oneYield 92%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 1-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one (Intermediate 13, 2.6 g, 10 mmol)) in i-Pr2NEt (28 mL) was added chloromethylmethyl ether (4.8 mL, 63 mmol). The mixture was stirred at ambient temperature for overnight, was quenched with 1M HCl, and extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (3% EtOAc-hexane) to give the title compound as a white solid (2.79 g, 92%).

Workup

  1. customwas quenched with 1M HCl
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (3% EtOAc-hexane)

Sources & evidence

ORD record
ord-d6166244a1a5495b9dbbe74df0592e23
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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