Water → HCID 18401890, compound

HRID 1018660Notes

Reaction equation

HRID 1018660 reaction equation
[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:12].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.O>CN(C=O)C>[CH:21]1([CH2:20][O:12][C:2]2[CH:3]=[CH:4][C:5]3[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[CH:1]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 108882361659-93-4

Product 1

HCID 18401890HCID 18401890, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (Helvetica Chimica Acta 1947, 1883.) (9.9 g, 61.0 mmol) and Cs2CO3 (26.3 g, 73.2 mmol) in DMF (100 ML) was added (bromomethyl)cyclohexane (10.2 mL, 73.2 mmol). The mixture was heated to 60° C. for 18 h, dumped into water and extracted with ethyl acetate. The combined extracts were washed with water, dried over magnesium sulfate and concentrated to a solid. The solid was recrystallized from ethanol (13.0 g, 83%). m.p. 62-63° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to a solid
  5. customThe solid was recrystallized from ethanol (13.0 g, 83%)

Sources & evidence

ORD record
ord-75597b37e63141ccac0cacb19b604733
Source dataset
uspto-grants-2002_11
Patent number
US06482852B2

Reaction notes

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