Water → 4-Hydroxy-4-(3-bromopropyl)-3.5-dimethyl-2,5-heptadiene

HRID 1603182Notes

Reaction equation

HRID 1603182 reaction equation
Br[C:2](=[CH:4][CH3:5])[CH3:3].[Li].[Br:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=O.O>CCCCC>[OH:13][C:11]([CH2:10][CH2:9][CH2:8][Br:7])([C:2]([CH3:3])=[CH:4][CH3:5])[C:4]([CH3:5])=[CH:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 209102-Bromobut-2-eneHCID 76300Ethyl 4-bromobutyrateHCID 3028194Lithium

Product 1

HCID 537997004-Hydroxy-4-(3-bromopropyl)-3.5-dimethyl-2,5-heptadiene

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
-10 °C

Procedure

Analogously to example I, 2-lithium-2-butene was prepared from 2-bromo-2-butene (15.0 g; 0.11 mol) and lithium (2.8 g; 0.26 mol). To the product obtained, ethyl 4-bromobutanoate (11.0 g; 0.056 mol) was added dropwise and with reflux at -40-20° C., followed by stirring for 30 minutes at -20° C. Water (200 ml) and subsequently pentane (100 ml) were slowly added dropwise at -20° C. After separation of the layers the water layer was washed two times with 100 ml of pentane/ether (1/1, v/v), after which the combined organic layers were washed with water (50 ml). The organic layer was dried (K2CO3), filtered and evaporated. The yield was 14.0 g (96%).

Workup

  1. customTo the product obtained
  2. customAfter separation of the layers the water layer
  3. washwas washed two times with 100 ml of pentane/ether (1/1
  4. washv/v), after which the combined organic layers were washed with water (50 ml)
  5. dry with materialThe organic layer was dried (K2CO3)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-65561c2dc6bd4190b9fd4713bd238471
Source dataset
uspto-grants-1999_11
Patent number
US05986029

Reaction notes

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