Diiodomethane → HCID 86730688, compound

HRID 2174634Notes

Reaction equation

HRID 2174634 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([OH:32])[CH2:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C([Zn][CH2:36][CH3:37])C.ICI.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.CCCCCC>[CH2:24]([O:23][CH2:22][CH:21]([OH:32])[CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:10][CH:11]1[CH2:12][CH:13]1[CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:36][CH3:37])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 6346DiiodomethaneHCID 24436Sodium SulfateHCID 86730689HCID 86730689, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 86730688HCID 86730688, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×

Procedure

A solution of 1-[(9Z,12Z)-octadeca-9,12-dien-1-yloxy]-3-(octyloxy)propan-2-ol in DCM (166 ml) in a 1 L flask under nitrogen was cooled in an ice/IPA bath (−15° C.) and then 1 M diethylzinc in hexane (199 ml, 199 mmol) added, followed by diiodomethane (24.05 ml, 298 mmol). The mixture was allowed to stir in the cooling bath overnight to gradually come up to room temperature. Reaction was quenched by addition of excess saturated ammonium chloride. Washed reaction into 2 L separatory funnel with hexane and water and added excess hexane, shook vigorously. Discarded lower aqueous layer, dried organic layer with sodium sulfate and evaporated to 1-(octyloxy)-3-[(8-{2-[(2-pentylcyclopropyl)methyl]cyclopropyl}octyl)oxy]propan-2-ol (15.5 g, 32.2 mmol, 97% yield) as a yellow oil. Material was used with no further purification. MS (ESI): 481 [M+H]+.

Workup

  1. customto gradually come up to room temperature
  2. customReaction
  3. customwas quenched by addition of excess saturated ammonium chloride
  4. washWashed
  5. customreaction into 2 L separatory funnel with hexane and water
  6. stirringshook vigorously

Sources & evidence

ORD record
ord-624ee9b673e64ea2b45f295751f271fb
Source dataset
uspto-grants-2015_06
Patent number
US09062021B2

Reaction notes

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