Carbon Dioxide → 157122-41-3

HRID 2379765Notes

Reaction equation

HRID 2379765 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][O:8][CH2:9]2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.CCCCC.[C:22](=[O:24])=[O:23].[K+].[Br-]>C1COCC1>[C:22]([C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][O:8][CH2:9]2)=[CH:4][CH:3]=1)([OH:24])=[O:23]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 8003PentaneHCID 253877Potassium BromideHCID 105605257-bromoisochromanHCID 178418306HCID 178418306, compound

Product 1

HCID 18956352157122-41-3

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 7-bromoisochroman (7 g; 32.86 mmol) in THF (100 ml) was cooled to -78° C. and treated with 40.6 ml of a 1.7M solution of tert-butyllithium in pentane (69 mmol; 2.1 eq). Powdered dry ice (excess) was added to the red anion solution within 45 seconds. The reaction mixture was stirred for 30 minutes at -78° C. and 1 hour at room temperature. The reaction was quenched with 60 ml of 1N HCl and extracted with 3×70 ml of ether. The ether layers were combined and washed with brine until the pH was neutral, dried with MgSO4, and concentrated in vacuo. The product was obtained as a white solid, mp 140°-142° C. (5.7 g; 82%). 1H NMR (CDCl3): δ2.95 (t, 2H); 4.03 (t, 2H); 4.83 (s, 2H); 7.24 (t, 1H); 7.89 (s, 1H); 7.92 (d, 1H). IR (KBr): 2954, 2561, 1684, 1427, 1293, 1108 cm-1.

Workup

  1. customThe reaction was quenched with 60 ml of 1N HCl
  2. extractionextracted with 3×70 ml of ether
  3. washwashed with brine until the pH
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product was obtained as a white solid, mp 140°-142° C. (5.7 g; 82%)

Sources & evidence

ORD record
ord-bba04b22345544d6a207088baf51c5ee
Source dataset
uspto-grants-1994_11
Patent number
US05364876

Reaction notes

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