Hydrochloric Acid → 1-Adamantylphosphine

HRID 1724105Notes

Reaction equation

HRID 1724105 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]12([P:17](Cl)(Cl)=O)[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.Cl>C1COCC1>[C:7]12([PH2:17])[CH2:14][CH:13]3[CH2:12][CH:11]([CH2:10][CH:9]([CH2:15]3)[CH2:8]1)[CH2:16]2

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 64195Phosphonic dichloride, tricyclo(3.3.1.1(sup 3,7))dec-1-yl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 117689541-Adamantylphosphine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (3.5 g, 74 mmol) was added over 2 hours to a cooled solution (0° C.) of 1-adamantylphosphonic acid dichloride (15 g, 59 mmol) in THF (250 cm3). The reaction was then allowed to warm to ambient temperature and was stirred for 20 hours. The grey suspension was then cooled (0° C.) and HCl (75 cm3, 1M) was slowly added via syringe, to afford a two phase system with some solid present in the lower phase. Concentrated HCl (8 cm3, 11M) was then added to improve the separation of the two layers. The (upper) THF phase was removed via cannula and dried over magnesium sulphate. After filtration via cannula, the volatiles were removed in-vacuo to afford the product.

Workup

  1. additionwas slowly added via syringe
  2. customto afford a two phase system with some solid present in the lower phase
  3. customthe separation of the two layers
  4. customThe (upper) THF phase was removed via cannula
  5. dry with materialdried over magnesium sulphate
  6. filtrationAfter filtration via cannula
  7. customthe volatiles were removed in-vacuo
  8. customto afford the product

Sources & evidence

ORD record
ord-9b8335cb1ca54e2e9b49cc08039f45b8
Source dataset
uspto-grants-2009_02
Patent number
US07485739B2

Reaction notes

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