Borane → HCID 11108066, compound

HRID 2198481Notes

Reaction equation

HRID 2198481 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.B.[CH:8]1([BH:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C#CCCCC>O1CCCC1>[CH:15](/[B:14]([CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:16]\[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 6331BoraneHCID 8079CyclohexeneHCID 127321-HexyneHCID 15879360CID 15879360

Product 1

HCID 11108066HCID 11108066, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 64 g (785.0 mmol) of cyclohexene in 20 ml of tetrahydrofuran (THF) is added to 392.5 ml (392.5 mmol) of borane (1 M solution in THF) at -15°, after which the solution is stirred at 0°-5° for 1 hour to prepare dicyclohexylborane. This is cooled to -15° and 32 g (392.5 mmol) of 1-hexyne in 10 ml of THF is added dropwise. After addition is completed the reaction mixture is stirred at 0°-5° for 2.5 hours to yield a solution of (E)-1-hexen-1-yldicyclohexylborane.

Workup

  1. temperatureThis is cooled to -15°
  2. additionAfter addition
  3. stirringis stirred at 0°-5° for 2.5 hours

Sources & evidence

ORD record
ord-c32c0d9787b64e85bd67cae17762eb01
Source dataset
uspto-grants-1982_11
Patent number
US04357474

Reaction notes

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