Ammonia → HCID 20308047, compound

HRID 1287288Notes

Reaction equation

HRID 1287288 reaction equation
N.[C:2]([CH2:5][C:6]12[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH:7]2O)([OH:4])=[O:3].[Li].C(O)C>C1COCC1>[C:2]([CH2:5][C:6]12[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:13]1[CH2:12][CH:11]=[CH:10][CH2:9][C:8]=1[CH2:7]2)([OH:4])=[O:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 3028194LithiumHCID 20308031HCID 20308031, compound

Product 1

HCID 20308047HCID 20308047, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 500 ml of liquid NH3 is added a solution of 9.84 g (0.04 mole) of 9a-carboxymethyl-1,2,3,4,4a,9a-hexahydrofluoren-9-ol (JACS 82 2561 (1960)) in 100 ml of THF. The mixture is then treated portionwise with 7 g of lithium cut in small pieces followed dropwise by sufficient absolute ethanol to discharge the blue color. After NH3 has evaporated, the cooled mixture is treated with water and carefully acidified. The desired 9a-carboxymethyl-1,2,3,4,5,8,4a,9a-octahydrofluorene is isolated by extraction with ether, drying and solvent removal.

Workup

  1. customAfter NH3 has evaporated
  2. additionthe cooled mixture is treated with water

Sources & evidence

ORD record
ord-bbca4d48e3364aa085381c3307a3780b
Source dataset
uspto-grants-1976_10
Patent number
US03984419

Reaction notes

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