Water → HCID 19353170, compound

HRID 378221Notes

Reaction equation

HRID 378221 reaction equation
Br[C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:25][C:26]1([CH3:42])[CH2:35][CH2:34][C:33]([CH3:37])([CH3:36])[C:32]2[CH:31]=[C:30]([C:38](=C)[CH2:39]O)[CH:29]=[CH:28][C:27]1=2.O>C(OCC)C.CCCCCCC.C(OCC)(=O)C>[Br:5][CH2:2][C:38]([C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[C:26]([CH3:42])([CH3:25])[CH2:35][CH2:34][C:33]2([CH3:37])[CH3:36])=[CH2:39]

Participants

8

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19353138HCID 19353138, compound

Product 1

HCID 19353170HCID 19353170, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

Tetrabromomethane (1.21 g, 3.8 mmol) is added to a mixture of triphenylphosphine (970 mg, 3.8 mmol) in ethyl ether (20 ml). A solution of 2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-ol (300 mg, 1.2 mmol) in ethyl ether (2 ml) is added. Stirring is continued for 24 h, then the reaction mixture is treated with water and ethyl acetate. The organic phase is washed with water and then concentrated in vacuo in a rotary evaporator. The oil obtained is taken up in heptane and filtered through silica. The filtrate is concentrated in vacuo in a rotary evaporator.

Workup

  1. washThe organic phase is washed with water
  2. concentrationconcentrated in vacuo in a rotary evaporator
  3. customThe oil obtained
  4. filtrationfiltered through silica
  5. concentrationThe filtrate is concentrated in vacuo in a rotary evaporator

Sources & evidence

ORD record
ord-9dc148f4cc7c41b68add2e7041d3acb0
Source dataset
uspto-grants-2000_02
Patent number
US06030952

Reaction notes

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