2-Bromopropane → HCID 54298051, compound

HRID 1578819Notes

Reaction equation

HRID 1578819 reaction equation
[CH3:1][CH:2]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:25])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:24])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH:3]=[O:4].C(Br)(C)C.[Mg].[C:31]([O:34][C:35](C)(C)[CH3:36])(=[O:33])[CH3:32].[Cl-].[NH4+]>CCOCC>[CH3:1][CH:2]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:25])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:24])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH:3]([OH:4])[CH2:32][C:31]([O:34][CH2:35][CH3:36])=[O:33]

Participants

7

Reactant 5

HCID 63582-BromopropaneHCID 10908tert-Butyl acetateHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 53893019HCID 53893019, compound

Product 1

HCID 54298051HCID 54298051, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of ether (344 ml) and 2,6,10,14,18-pentamethyl-5,9,13,17-nonadecatetraenal (34.4 g), Grignard reagent (prepared by adding portionwise isopropyl bromide (18.5 g) to a mixture of ether (100 ml) and metallic magnesium (3.7 g), adding further t-butyl acetate (17.4 g) thereto while cooling with ice and then stirring the resultant mixture for 1 hour) is dropwise added while cooling with ice. The resultant mixture is stirred at room temperature for 3 hours, and the reaction mixture is poured into an aqueous saturated solution of ammonium chloride. The ether layer is separated, washed with water, dried and evaporated. The residual material is chromatographed on silica gel (500 g) using a mixture of benzene and ethyl acetate (9.5:0.5 by weight) to give ethyl 3,7,11,15,19-pentamethyl-6,10,14,18-eicosatetraen-2-ol-1-carboxylate (28.5 g) as a pale yellow oil. IR: 3480, 1030 cm-1 (OH); 1720, 1180 cm-1 (COO).

Workup

  1. customprepared
  2. temperaturewhile cooling with ice
  3. additionis dropwise added
  4. temperaturewhile cooling with ice
  5. customThe ether layer is separated
  6. washwashed with water
  7. customdried
  8. customevaporated
  9. customThe residual material is chromatographed on silica gel (500 g)
  10. additiona mixture of benzene and ethyl acetate (9.5:0.5 by weight)

Sources & evidence

ORD record
ord-dc895352005e4083b0af13089aa2dfcf
Source dataset
uspto-grants-1976_02
Patent number
US03939202

Reaction notes

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