Tributylphosphine → (R/S) Ethyl 2-(6-(2,3-dihydro-1H-inden-2-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)acetate

HRID 731185Notes

Reaction equation

HRID 731185 reaction equation
C(P(CCCC)CCCC)CCC.CN(C(/N=N/C(N(C)C)=O)=O)C.[CH2:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH:27]1[OH:35].[CH2:36]([O:38][C:39](=[O:52])[CH2:40][CH:41]1[C:50]2[C:45](=[CH:46][C:47](O)=[CH:48][CH:49]=2)[CH2:44][CH2:43][CH2:42]1)[CH3:37]>C1C=CC=CC=1>[CH2:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH:27]1[O:35][C:47]1[CH:46]=[C:45]2[C:50](=[CH:49][CH:48]=1)[CH:41]([CH2:40][C:39]([O:38][CH2:36][CH3:37])=[O:52])[CH2:42][CH2:43][CH2:44]2

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 779362-IndanolHCID 5353800DiamideHCID 57835772Ethyl 2-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetate

Product 1

HCID 57835728(R/S) Ethyl 2-(6-(2,3-dihydro-1H-inden-2-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tributyl phosphine (137 mg, 0.68 mmol) and TMAD (122 mg, 0.68 mmol) were added successively to a dry benzene (10 mL) solution of 2-indanol (92 mg, 0.68 mmol) and ethyl 2-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetate 52.5 (160 mg, 0.68 mmol) with stirring under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2 days. The product was isolated by silica gel column chromatography after filtration and evaporation of the solvent in vacuo. (R/S)-Ethyl 2-(6-(2,3-dihydro-1H-inden-2-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)acetate (52) was obtained as a colorless oil (85 mg, 35%). LC-MS ESI (pos.) m/e: 351 (M+H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 days
  2. customThe product was isolated by silica gel column chromatography
  3. filtrationafter filtration and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-21c5694febe5434c96d24875121e642d
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

Loading…