Chloromethyl Methyl Ether → HCID 68704317, compound

HRID 732316Notes

Reaction equation

HRID 732316 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@H:7]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C@@H:6]1[CH2:19][CH2:20][C:21](=[O:23])[CH2:22][C@H:5]21.CC(C)([O-])C.[K+].[CH3:30][O:31][CH2:32]Cl.C1[CH2:38][O:37][CH2:36]C1>>[CH3:30][O:31][CH2:32][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:36][O:37][CH3:38])=[CH:16][CH:17]=1)[CH:6]1[CH2:19][CH2:20][C:21](=[O:23])[CH2:22][CH:5]21

Participants

5

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 11162677HCID 11162677, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 68704317HCID 68704317, compound

Procedure

To a 0 C solution of Example 19 (0.100 g, 0.32 mmol) in THF (3 mL) add potassium tert-butoxide (0.090 g, 0.81 mmol) followed by methoxymethyl chloride (MOM-Cl) (0.061 mL, 0.81 mmol). Remove the ice bath and stir for 1 h at room temperature. Pour the contents into ½ satd. NaHCO3 (50 mL) and extract with Et2O (2×25 mL) and EtOAc (2×25 mL). Wash the combine organic extracts with brine (50 mL), dry over Na2SO4, and concentrate to afford a brown residue. Purify the residue by MPLC (0% to 25% to 50% EtOAc/hexanes) to afford Preparation 35 (0.102 g, 80%). 1H NMR (CDCl3) δ 7.37 (d, J=8.4 Hz, 2H), 7.09 (d, J=8.4 Hz, 2H), 6.96 (d, J=2.4 Hz, 1H), 6.87 (dd, J=2.4, 8.8 Hz, 1H), 6.84 (d, J=8.8 Hz, 1H), 5.28 (s, 1H), 5.20 (s, 2H), 5.13 (A of AB, JAB=7.0 Hz, 1H), 5.07 (B of AB, JAB=7.0 Hz, 1H), 3.87 (m, 1H), 3.50 (s, 3H), 3.48 (s, 3H), 3.04 (br d, J=14.4 Hz, 1H), 2.79 (dd, J=6.2, 14.4 Hz, 1H), 2.46 (m, 1H), 2.21 (m, 2H), 1.62-1.79 (m, 2H).

Workup

  1. customRemove the ice bath
  2. additionPour the contents into ½ satd
  3. extractionNaHCO3 (50 mL) and extract with Et2O (2×25 mL) and EtOAc (2×25 mL)
  4. washWash the combine organic extracts with brine (50 mL)
  5. dry with materialdry over Na2SO4
  6. concentrationconcentrate
  7. customto afford a brown residue
  8. customPurify the residue by MPLC (0% to 25% to 50% EtOAc/hexanes)
  9. customto afford

Sources & evidence

ORD record
ord-5817f97e19af4b0bbd42415cd6917141
Source dataset
uspto-grants-2009_09
Patent number
US07585985B2

Reaction notes

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