Chloromethyl Methyl Ether → HCID 123856196, compound

HRID 530277Notes

Reaction equation

HRID 530277 reaction equation
[Si:1]([O:8][C@H:9]([CH3:21])[CH2:10][CH2:11][C@@H:12]([OH:20])/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:22](Cl)[O:23][CH3:24].CCN(C(C)C)C(C)C>C(Cl)Cl>[Si:1]([O:8][C@H:9]([CH3:21])[CH2:10][CH2:11][C@@H:12]([O:20][CH2:22][O:23][CH3:24])/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 57342763HCID 57342763, compound

Product 1

HCID 123856196HCID 123856196, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the compound (30, ethyl(4R,7R,E)-7-((tert-butyldimethylsilyl)oxy)-4-hydroxyoct-2-enoate) in dry CH2Cl2 solvent, MOMCl (2 equiv), DIPEA (3 equiv) were added and stirred for 8 h. On completion of the reaction (by checking TLC), the organic layer was extracted in DCM, washed with brine, dried over anhydrous Na2SO4. The solvent was removed in vacuum, concentrated and subjected for chromatographic separation. The eluent was allowed to come in a solution of pet ether:EtOAC=90:10 as a pale yellow liquid [α]25=+23.22 (c 1.24, CHCl3); 1H NMR (200 MHz, CDCl3): δ 6.69-6.80 (dd, 1H), 5.96 (d, 1H), 4.57 (m, 2H), 4.14 (m, 3H), 3.81 (m, 1H), 1.40 (t, 3H), 1.23 (d, 2H), 0.84 (s, 9H), −0.4 (s, 6H); 13C NMR (CDCl3, 50 MHz): 166.04, 147.76, 121.95, 94.48, 75.04, 68.07, 60.37, 55.55, 34.94, 30.78, 25.92, 23.85, 18.12, 14.28, −4.29; −4.67.

Workup

  1. customOn completion of the reaction (
  2. extractionwas extracted in DCM
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed in vacuum
  6. concentrationconcentrated
  7. customsubjected for chromatographic separation

Sources & evidence

ORD record
ord-1d84c0f22328427abe48ea90dad22bf6
Source dataset
uspto-grants-2016_05
Patent number
US09353077B2

Reaction notes

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