Hydrochloric Acid → HCID 23436668, compound

HRID 992782Notes

Reaction equation

HRID 992782 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].O1[CH2:11][CH2:10][CH2:9][CH2:8]1.[C:12]12(C3C(=C)C=CC=3)[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.Cl.[CH2:29](OCC)C>O>[CH:14]12[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][CH:12]([CH2:21]3)[CH:13]1[C:8]1[CH2:29][CH:11]=[CH:10][CH:9]=1)[CH2:20]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 86588815HCID 86588815, compound

Product 1

HCID 23436668HCID 23436668, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 500 mL argon-purged round bottom flask was charged with LiAlH4 (8.20 g, 216 mmol) and 100 mL tetrahydrofuran. Adamantylfulvene (30.00 g, 151.3 mmol) was added via solid addition funnel, followed by another 100 mL tetrahydrofuran over 2 minutes at 0° C. After stirring for 22 hours at room temperature, the reaction was cooled to 0° C. and 100 mL water were added dropwise over 60 minutes. Then, 100 mL concentrated aqueous HCl in 300 mL water and 50 mL diethyl ether were added. The organic layer was isolated and the aqueous layer extracted with diethyl ether (3×50 mL). The combined organic layers were dried over MgSO4, filtered, and rotavapped to give 30.30 g of product in quantitative yield. MS (GC-MS) m/z 200.3 (M+).

Workup

  1. customA 500 mL argon-purged round bottom flask
  2. temperaturethe reaction was cooled to 0° C.
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer extracted with diethyl ether (3×50 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-547bebee9595481183ff4516032e8776
Source dataset
uspto-grants-2002_10
Patent number
US06469188B1

Reaction notes

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