(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile → HCID 86740316, compound

HRID 1639436Notes

Reaction equation

HRID 1639436 reaction equation
[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:13])[O:8][CH2:9][CH:10]([Cl:12])[Cl:11])[C@H:3]1[C:14]([OH:16])=[O:15].[C:18]([C@@H:20](O)[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1)#[N:19]>>[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:13])[O:8][CH2:9][CH:10]([Cl:11])[Cl:12])[C@H:3]1[C:14]([O:16][C@H:20]([C:18]#[N:19])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:22]=1)=[O:15]

Participants

3

Reactant 2

HCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 70420167HCID 70420167, compound

Product 1

HCID 86740316HCID 86740316, compound

Procedure

Using the procedure of Step F of Example 9, 3 g of the product of Step B and 2.25 g of (S)α-cyano-3-phenoxy-benzyl alcohol were reacted to obtain after elution with 8-3 and 9-1 mixtures of cyclohexane-ethyl acetate 1.6 of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(2,2-dichloroethoxy(-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+54°±2° (c=1% in benzene).

Workup

  1. customwere reacted
  2. customto obtain
  3. washafter elution with 8-3 and 9-1 mixtures of cyclohexane-ethyl acetate 1.6 of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(2,2-dichloroethoxy(-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+54°±2° (c=1% in benzene)

Sources & evidence

ORD record
ord-839366d80d2e45e7b452a6dbe842a420
Source dataset
uspto-grants-1989_11
Patent number
US04883806

Reaction notes

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