Tetrahydrofuran → HCID 86707572, compound

HRID 2279966Notes

Reaction equation

HRID 2279966 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][O:41][CH2:42][O:43][CH2:44][CH3:45])=[CH:34][CH:33]=3)[CH:22]=[C:23]([O:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[CH:24]=2)=[CH:15][C:14]=1[F:46])C1C=CC=CC=1.C1C[O:50][CH2:49]C1>[Pd]>[F:46][C:14]1[CH:15]=[C:16]([C:19]2[CH:20]=[C:21]([C:32]3[CH:33]=[CH:34][C:35]([O:38][CH2:39][CH2:40][O:41][CH2:42][O:43][CH2:44][CH2:45][O:50][CH3:49])=[CH:36][CH:37]=3)[CH:22]=[C:23]([O:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[CH:24]=2)[CH:17]=[CH:18][C:13]=1[O:12][CH2:11][CH2:10][CH2:9][OH:8]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 118362022HCID 118362022, compound

Product 1

HCID 86707572HCID 86707572, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2.60 g (4.20 mmol) 4″-(3-benzyloxy-propoxy)-3″-fluoro-5′-(2-methoxy-ethoxymethoxy)-4-(2-ethoxymethoxy-ethoxy)-[1,1′;3′,1″]terphenyl are hydrogenated in 50 ml THF on 1.0 g Pd/activated charcoal until the reaction is completed. The catalyst is filtered off and the solvent is removed in vacuo. 3-{3″-fluoro-5′-(2-methoxy-ethoxymethoxy)-4-[2-(2-methoxy-ethoxymethoxy)-ethoxy]-[1 1′;3′,1″]terphenyl-4″-yloxy}-propane-1-ol is obtained as colourless oil, which is used for the next step without further purification.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is removed in vacuo
  3. custom3-{3″-fluoro-5′-(2-methoxy-ethoxymethoxy)-4-[2-(2-methoxy-ethoxymethoxy)-ethoxy]-[1 1′;3′,1″]terphenyl-4″-yloxy}-propane-1-ol is obtained as colourless oil, which
  4. customis used for the next step without further purification

Sources & evidence

ORD record
ord-ecdfd86b34704d7bb0aa7cafa97649d7
Source dataset
uspto-grants-2015_09
Patent number
US09133395B2

Reaction notes

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