2-Iodothiophene → (S)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(2-thienyl)ethynyl]-2H-1-benzopyran-6-ol

HRID 256835

Reaction equation

HRID 256835 reaction equation
[C:1]([C@:3]1([CH3:17])[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1)#[CH:2].I[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1>>[CH3:17][C@@:3]1([C:1]#[C:2][C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1

Participants

3

Reactant 2

HCID 189212-IodothiopheneHCID 9859440(S)-2-ethynyl-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol

Product 1

HCID 15171811(S)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(2-thienyl)ethynyl]-2H-1-benzopyran-6-ol

Procedure

This enantiomer was obtained as described in Example 4 by reacting the (S)-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol from Example 11 with 2-iodothiophene. It was isolated by chromatography as above and was crystallized from ether/hexane to yield colorless crystals with m.p. 131°-134° C. [α]D25 =+34.9° (c=1.145 in MeOH).

Workup

  1. customThis enantiomer was obtained
  2. customIt was isolated by chromatography as above and
  3. customwas crystallized from ether/hexane
  4. customto yield colorless crystals with m.p. 131°-134° C. [α]D25 =+34.9° (c=1.145 in MeOH)

Sources & evidence

ORD record
ord-d6d337da984d4863b978dfb806adf55f
Source dataset
uspto-grants-1993_11
Patent number
US05260294

Linked notes

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