Benzene → HCID 66859378, compound

HRID 255155Notes

Reaction equation

HRID 255155 reaction equation
O[C@]1([C:12]([OH:14])=[O:13])CCC(CO)(C)C1(C)C.[CH2:15]([CH2:18]OC)OC.O.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25](S(O)(=O)=O)=[CH:24][CH:23]=1.[CH3:33][O:34][CH2:35][O:36][CH3:37].[CH:38]1C=CC=CC=1>>[CH2:15]([C:27]12[C:22]([CH2:23][CH3:24])([CH2:32][CH3:38])[C@@:37]([C:12]([OH:14])=[O:13])([CH2:25][CH2:26]1)[O:36][CH2:35][O:34][CH2:33]2)[CH3:18]

Participants

6

Reactant 5

HCID 241BenzeneHCID 8020DimethoxymethaneHCID 80711,2-DimethoxyethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 66858910HCID 66858910, compound

Product 1

HCID 66859378HCID 66859378, compound

Procedure

A mixture of Example 222A (131.6 mg), dimethoxyethane (0.575 mL) and para-toluenesulfonic acid monohydrate (catalytic) in benzene (15 mL) was stirred and heated to reflux with a Dean-Stark trap overnight. An additional 0.5 mL dimethoxymethane was added and heating continued 24 hours. The reaction mixture was evaporated to dryness and flash chromatographed over silica gel eluting with 10% methanol/CH2Cl2 to afford the title compound 1H NMR (CDCl3, 300 MHz) δ ppm 0.88 (s, 3H), 0.94 (s, 3H), 1.15 (s, 3H), 1.88-2.05 (m, 3H), 2.7-2.85 (m, 1H), 3.59 (s, 2H), 5.00 (AB q, J=26.3, 7.9 Hz, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux with a Dean-Stark trap overnight
  3. temperatureheating
  4. customThe reaction mixture was evaporated to dryness and flash
  5. customchromatographed over silica gel eluting with 10% methanol/CH2Cl2

Sources & evidence

ORD record
ord-1a217a63b8044deeb2fea537b4d868d6
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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