Triethylamine → HCID 10381747, compound

HRID 465618Notes

Reaction equation

HRID 465618 reaction equation
[CH2:1]([C@@H:4]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][OH:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([O:6][CH2:5][C@@H:4]([CH2:1][CH:2]=[CH2:3])[CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10243752HCID 10243752, compound

Product 1

HCID 10381747HCID 10381747, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (-)-2(R)-allyl-6-(benzyloxy)-hexan-1-ol (5.0 g, 20 mmol) in methylene chloride (85 ml) at 0° C. is added triethylamine (4.6 ml, 33 mmol) followed by methanesulfonyl chloride. The mixture is allowed to stir at 0° C. for 2 hours and then quenched using saturated sodium bicarbonate solution. The organic layer is separated, dried, filtered and evaporated to give (-)-2(R)-allyl-6-(benzyloxy)hexan-1-yl methanesulfonate (mesylate ester) which is used as is.

Workup

  1. customquenched
  2. customThe organic layer is separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-8632f73dad394befabc52ae4b6d9483d
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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